Summary
The construction of small synthetic proteins that bind only one or a small number of (bacterio)chlorophylls ((B)Chls) is a powerful approach to understand the concepts and guidelines of protein-(B)Chl interactions and assembly; the systems can be extended, in a stepwise fashion, by adding other cofactors or by oligomerization. We review the unique aspects of the de novo design and construction of (B)Chl-binding proteins, and describe recent progress and challenges in designing new BChl-protein platforms for delineating general rules and guidelines of (B)Chl-protein assembly, structure, and function. The relevant aspects of chlorophyll (Chl) and BChl chemical structures are outlined, as well as the modes of interactions with natural proteins. Two distinct strategies are then described for designing de novo water-soluble (B)Chl-binding proteins. The first strategy is based on the covalent assembly of modular four-helix bundle proteins, the second follows the original non-covalent heme-binding protein maquette design, which relies on self-assembly of amphiphilic helices that is primarily driven by the hydrophobic effect. Finally, we demonstrate the extension of the latter to designing transmembrane-like versions of (B)Chl-protein maquettes.
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Abbreviations
- AP:
-
amphiphilic
- BChl:
-
bacteriochlorophyll
- BChlide:
-
bacteriochlorophyllide
- BPhe:
-
bacteriopheophytin
- BPheide:
-
bacteriopheophorbide
- CD:
-
circular dichroism
- Chi:
-
chlorophyll
- Chlide:
-
chlorophyllide
- HP:
-
hydrophilic
- LP:
-
lipophilic
- [M]-(B)Chlide:
-
(B)Chlide in which the central metal has been replaced by metal ‘M’
- MOP:
-
modular organized protein
- NIR:
-
near infrared
- Phe:
-
pheophytin
- RC:
-
reaction center
- UV:
-
ultraviolet
- Vis:
-
visible
References
Agostiano A, Cosma P, Trotta M, Monsu-Scolaro L and Micali N (2002) Chlorophyll a behavior in aqueous solvents: Formation of nanoscale self-assembled complexes. J Phys Chem B 106: 12820–12829
Balaban TS, Linke-Schaetzel M, Bhise AD and Vanthuyne N and Roussel C (2004) Green self-assembling porphyrins and chlorins as mimics of the natural bacteriochlorophylls c, d, and e. Eur J Org Chem 2004: 3919–3930
Barker PD (2003) Designing redox metalloproteins from bottom-up and top-down perspectives. Curr Op Struct Biol 13: 490–499
Ben-Shem A, Nelson N and Frolow F (2003) Crystallization and initial X-ray diffraction studies of higher plant Photosystem I. Acta Crystallogr D Biol Crystallogr 59: 1824–1827
Biesiadka J, Loll B, Kern J, Irrgang K-D and Zouni A (2004) Crystal structure of cyanobacterial Photosystem II at 3.2 Å resolution: A closer look at the Mn cluster. Phys Chem Chem Phys 6: 4733–4736
Bowie JU (2000) Understanding membrane protein structure by design. Nature Struct Biol 7: 92–94
Boxer SG, Kuki A, Wright KA, Katz BA and Xuong N (1982) Oriented properties of the chlorophylls — electronic absorption-spectroscopy of orthorhombic pyrochlorophyllide α-apomyglobin single-crystals. Proc Natl Acad Sci USA 79: 1121–1125
Buchler JW (1975) Static coordination chemistry of metalloporphyrins. In: Smith KM (ed) Porphyrins and Metalloporphyrins, pp 157–232. Elsevier, Amsterdam
Butterfield SM and Waters ML (2003) A designedhairpin peptide for molecular recognition of ATP in water. J Am Chem Soc 125: 9580–9581
Chen M, Eggink LL, Hoober JK and Larkum AW (2005) Influence of structure on binding of chlorophylls to peptide ligands. J Am Chem Soc 127: 2052–2053
Cochran FV, Wu SP, Wang W, Nanda V, Saven JG, Therien MJ and DeGrado WF (2005) Computational de novo design and characterization of a four-helix bundle protein that selectively binds a nonbiological cofactor. J Am Chem Soc 127: 1346–1347
Coleman WJ and Youvan DC (1990) Spectroscopic analysis of genetically modified photosynthetic reaction centers. Ann Rev Biophys (Biophys Chem.) 19: 333–367
Davis CM, Parkes-Loach PS, Cook CK, Meadows KA, Bandilla M, Scheer H and Loach PA (1996) Comparison of the structural requirements for bacteriochlorophyll binding in the core light-harvesting complexes of Rhodospirillum rubrum and Rhodobacter sphaeroides using reconstitution methodology with bacteriochlorophyll analogs. Biochemistry 35: 3072–3084
De Jonge N, Rau HK and Haehnel W (1999) Light-induced electron transfer in synthetic metalloproteins. Z Phys Chem 213: 175–180
DeGrado WF, Wasserman ZR and Lear JD (1989) Protein design, a minimalist approach. Science 243: 622–628
Dieckmann GR, McRorie DK, Tierney DL, Utschig LM, Singer CP, O’Halloran TV Penner-Hahn JE, DeGrado WF and Pecoraro VL (1997) De novo design of mercury-binding two- and threehelical bundles. J Am Chem Soc 119: 6195–6196
Discher BM, Noy D, Strzalka J, Ye S, Moser CC, Lear JD, Blasie JK and Dutton PL (2005) Design of amphiphilic protein maquettes: controlling assembly, membrane insertion, and cofactor interactions. Curr Op Chem Biol 44: 12329–12343
Domanskii V, Rassadina V, Gus-Mayer S, Wanner G, Schoch S and Rüdiger W (2003) Characterization of two phases of chlorophyll formation during greening of etiolated barley leaves. Planta 216: 475–483
Dudkowiak A, Nakamura C, Arai T and Miyake J (1998) Interactions of chlorophyll a with synthesized peptide in aqueous solution. J Photochem Photobiol B 45: 43–50
Dudkowiak A, Kusumi T, Nakamura C and Miyake J (1999) Chlorophyll a aggregates stabilized by a synthesized peptide. J Photochem Photobiol. A 129: 51–55
Eggink LL and Hoober JK (2000) Chlorophyll binding to peptide maquettes containing a retention motif. J Biol Chem 275: 9087–9090
El-Kabbani O, Chang C-H, Tiede D, Norris J and Schiffer M (1991) Comparison of reaction centers from Rhodobacter sphaeroides and Rhodopseudomonas viridis: Overall architecture and protein-pigment interactions. Biochemistry 30: 5361–5369
Evans TA and Katz JJ (1975) Evidence for 5-and 6-coordinated magnesium in bacteriochlorophyll a from visible absorption spectroscopy. Biochim Biophys Acta 396: 414–426
Fahnenschmidt M, Bittl R, Rau HK, Haehnel W and Lubitz W (2000) Electron paramagnetic resonance and electron nuclear double resonance spectroscopy of a heme protein maquette. Chem Phys Lett 323: 329–339
Fahnenschmidt M, Rau HK, Bittl R, Haehnel W and Lubitz W (1999) Characterization of a de novo designed heme protein by EPR and ENDOR spectroscopy. Chem Eur J 5: 2327–2334
Ferreira KN, Iverson TM, Maghlaoui K, Barber J and Iwata S (2004) Architecture of the photosynthetic oxygen-evolving center. Science 303: 1831–1838
Fiedor L (2006) Hexacoordination of bacteriochlorophyll in photosynthetic antenna LH1. Biochemistry 45: 1910–1918
Fiedor L, Leupold D, Teuchner K, Voigt B, Hunter CN, Scherz A and Scheer H (2000) Excitation trap approach to analyze size and pigment-pigment coupling: Reconstitution of LH1 antenna of Rhodobacter sphaeroides with Ni-substituted bacteriochlorophyll. Biochemistry 40: 3737–3747.
Frank HA, Innes J, Aldema M, Neumann R and Schenck CC (1993) Triplet state EPR of reaction centers from the His(L173) → Leu(L 173) mutant of Rhodobacter sphaeroides which contains a heterodimer primary donor. Photosynth. Res. 38: 99–101.
Freer A, Prince S, Sauer K, Papiz M, Hawthornthwaite-Lawless A, McDermott G, Cogdell R and Isaacs NW (1996) Pigment, pigment interactions and energy transfer in the antenna complex of the photosynthetic bacterium Rhodopseudomonas acidophila. Structure 4: 449–462
Frigaard NU, Chew AGM, Maresca JA and Bryant DA (2006) Bacteriochlorophyll biosynthesis in green bacteria. In: Grimm B, Porra R, Rüdiger W and Scheer H (eds) Chlorophylls and Bacteriochlorophylls: Biochemistry, Biophysics, Functions and Applications (Advances in Photosynthesis and Respiration, Vol 25), pp 201–221. Springer, Dordrecht
Gall A, Cogdell RJ and Robert B (2003) Influence of carotenoid molecules on the structure of the bacteriochlorophyll binding site in peripheral light-harvesting proteins from Rhodobacter sphaeroides. Biochemistry 42: 7252–8
Garcia-Martin A, Kwa L, vonJan M and Braun P (2006) Assembly of novel bacteriochlorophyll proteins in the native lipid environment. In: Grimm B, Porra R, Rüdiger W and Scheer H (eds) Chlorophylls and Bacteriochlorophylls: Biochemistry, Biophysics, Functions and Applications (Advances in Photosynthesis and Respiration, Vol 25), pp 387–396. Springer, Dordrecht
Gentemann S, Medforth CJ, Forsyth TP, Nurco DJ, Smith KM, Fajer J and Holten D (1994) Photophysical properties of conformationally distorted metal-free porphyrins. Investigation into the deactivation mechanisms of the lowest excited singlet state. J Am Chem Soc 116: 7363–7368
Ghirlanda G, Osyczka A, Liu W, Antolovich M, Smith KM, Dutton PL, Wand AJ and DeGrado WF (2004) De novo design of a D 2-symmetrical protein that reproduces the diheme four-helix bundle in cytochrome bc 1 J Am Chem Soc 126: 8141–8147
Ghosh D, Lee KH, Demeler B and Pecoraro VL (2005) Linear free-energy analysis of mercury(II) and cadmium(II) binding to three-stranded coiled coils. Biochemistry 44: 10732–10740
Gibney BR, Mulholland SE, Rabanal F and Dutton PL (1996) Ferredoxin and ferredoxin-heme maquettes. Proc Natl Acad Sci USA 93: 15041–15046
Gibney BR, Rabanal F, Skalicky JJ, Wand AJ and Dutton PL (1999) Iterative protein redesign. J Am Chem Soc 121: 4952–4960
Gibney BR, Isogai Y, Rabanal F, Reddy KS, Grosset AM, Moser CC and Dutton PL (2000) Self-assembly of heme A and heme B in a designed four-helix bundle: Implications for a cytochrome c oxidase maquette. Biochemistry 39: 11041–11049
Grosset AM, Gibney BR, Rabanal F, Moser CC and Dutton PL (2001) Proof of principle in a de novo designed protein maquette: An allosterically regulated, charge-activated conformational switch in a tetra-alpha-helix bundle. Biochemistry 40: 5474–5487
Gudowska-Nowak E, Newton MD and Fajer J (1990) Conformational and environmental effects on bacteriochlorophyll optical spectra: Correlations of calculated spectra with structural results. J Phys Chem 94: 5795–5801
Haehnel W (2004) Chemical synthesis of TASP-arrays and their application in protein design. Mol Diversity 8: 219–229
Harbury PB, Zhang T, Kim PS and Alber T (1993) A switch between two-, three-, and four-stranded coiled coils in GCN4 leucine zipper mutants. Science 262: 1401–1407
Hartwich G, Fiedor L, Simonin I, Cmiel E, Schaefer W, Noy D, Scherz A and Scheer H (1998) Metal-substituted bacteriochlorophylls. 1. Preparation and influence of metal and coordination on spectra. J Am Chem Soc 120: 3675–3683
Ho SP and DeGrado WF (1987) Design of a 4-helix bundle protein: Synthesis of peptides which self-associate into a helical protein. J Am Chem Soc 109: 6751–6758
Hofmann E, Wrench PM, Sharpies FP, Hiller RG, Weite W and Diederichs K (1996) Structural basis of light-harvesting by carotenoids: peridinin-chlorophyll-protein from Amphidinium carterae. Science 272: 1788–1791
Horigome D, Satoh H, Itoh N, Mitsunaga K, Oonishi I, Nakagawa A and Uchida A (2007) Structural mechanism and photoprotective function of water-soluble chlorophyll-binding protein. J Biol Chem 282: 76525–6531
Huang SS, Gibney BR, Stayrook SE, Dutton PL and Lewis M (2003) X-ray structure of a maquette scaffold. J Mol Biol 326: 1219–1225
Huang SS, Koder RL, Lewis M, Wand AJ and Dutton PL (2004) The HP-1 maquette: From an apoprotein to a structured hemoprotein designed to promote redox-coupled proton exchange. Proc Natl Acad Sci USA 101: 5536–5541
Hübschmann T, Borner T, Hartmann E and Lamparter T (2001) Characterization of the Cph 1 holo-phytochrome from Synechocystis sp. PCC 6803. Eur J Biochem 268: 2055–2063
Ivancich A, Artz K, Williams JC, Allen JP and Mattioli TA (1998) Effects of hydrogen bonds on the redox potential and electronic structure of the bacterial primary electron donor. Biochemistry 37: 11812–11820
Iwata S, Lee JW, Okada K, Lee JK, Iwata M, Rasmussen B, Link TA, Ramaswamy S and Jap BK (1998) Complete structure of the 11-subunit bovine mitochondrial cytochrome bc 1 complex. Science 281: 64–71
Jordan P, Fromme P, Witt HT, Klukas O, Saenger W and Krauss N (2001) Three-dimensional structure of cyanobacterial Photosystem I at 2.5 Å resolution. Nature 411: 909–917
Kashiwada A, Watanabe H, Tanaka T and Nango M (2000) Molecular assembly of zinc bacteriochlorophyll a by synthetic hydrophobic 1α-helix polypeptides. Chem Lett 24–25
Katz E, Heleg-Shabtai V, Willner I, Rau HK and Haehnel W (1998) Surface reconstitution of a de novo synthesized hemoprotein for bioelectronic applications. Angew Chem Int Ed 37: 3253–3256
Katz JJ, Shipman LL, Cotton TM and Janson TR (1978) Chlorophyll aggregation: coordination interactions in chlorophyll monomers, dimers and oligomers. In: Dolphin D (ed) The Porphyrins. Physical Chemistry, Part C, pp 402–458. Academic Press, New York
Katz JJ, Bowman MK, Michalski TJ and Worcester DL (1991) Chlorophyll aggregation: Chlorophyll-water micelles as models for in vivo long-wavelength chlorophyll. In: Scheer H (ed) Chlorophylls, pp 211–236. CRC-Press, Boca Raton
Kennedy ML and Gibney BR (2002) Proton coupling to [4Fe-4S]2+ and [4Fe-4Se]2+ oxidation and reduction in a designed protein. J Am Chem Soc 124: 6826–6827
Klemba M, Gardner KH, Marino S, Clarke ND and Regan L (1995) Novel metal-binding proteins by design. Nature Struct Biol 2: 368–373
Koder RL and Dutton PL (2006) Intelligent design: The de novo engineering of proteins with specified functions. Dalton Transact 25: 3045–3051
Koder RL, VKG, Cerda J, Noy D, Smith KM, Wand AJ and Dutton PL (2006) Native-like structure in designed four α-helix bundles driven by buried polar interactions. J Am Chem Soc 128: 14450–14451
Kräutler B and Hörtensteiner S (2006) Chlorophyll catabolites and the biochemistry of chlorophyll breakdown. In: Grimm B, Porra R, Rüdiger W and Scheer H (eds) Chlorophylls and Bacteriochlorophylls: Biochemistry, Biophysics, Functions and Applications (Advances in Photosynthesis and Respiration, Vol 25), pp 237–260. Springer, Dordrecht
Kunieda M, Mizoguchi T and Tamiaki H (2004) Diastereoselective self-aggregation of synthetic 3-(1-hydroxyethyl)-bacteriopyrochlophyll a as a novel photosynthetic antenna model absorbing near the infrared regions. Photochem Photobiol 79: 55–61
Küpper H, Dedic R, Svoboda A, Hala J and Kroneck PM (2002) Kinetics and efficiency of excitation energy transfer from chlorophylls, their heavy metal-substituted derivatives, and pheophytins to singlet oxygen. Biochim Biophys Acta 1572: 107–113
Lapouge K, Näveke A, Sturgis JN, Hartwich G, Renaud D, Simonin I, Lutz M, Scheer H and Robert B (1998) Non-bonding molecular factors influencing the stretching wavenumbers of the conjugated carbonyl groups of bacteriochlorophyll a. J Raman Spectrosc 29: 977–981
Lear JD, Wasserman ZR and Degrado WF (1988) Synthetic amphiphilic peptide models for protein ion channels. Science 240: 1177–1181
Li WW, Hellwig P, Ritter M and Haehnel W (2006) De novo design, synthesis, and characterization of quinoproteins. Chem Eur J 12: 7236–7245
Liu Z, Yan H, Wang K, Kuang T, Zhang J, Gui L, An X and Chang W (2004) Crystal structure of spinach major light-harvesting complex at 2.72 Å resolution. Nature 428: 287–292
Lutz M and Mäntele W (1991) Vibrational spectroscopy of chlorophylls. In: Scheer H (ed) Chlorophylls, pp 855–902. CRC Press, Boca Raton, FL
Ma JG, Zhang J, Franco R, Jia SL, Moura I, Moura JJG, Kroneck PMH and Shelnutt JA (1998) The structural origin of nonplanar heme distortions in tetraheme ferricytochromes c 3. Biochemistry 37: 12431–12442
Macpherson A and Hiller R (2003) Light-harvesting Systems in Chl c-containing Algae. In: Green B and Parson W (eds) Light-Harvesting Antennas in Photosynthesis (Advances in Photosynthesis and Respiration, Vol 13), pp 323–352. Kluwer Academic Publishers, Dordrecht
Maglio O, Nastri F, Pavone V, Lombardi A and DeGrado WF (2003) Preorganization of molecular binding sites in designed diiron proteins. Proc Natl Acad Sci USA 100: 3772–3777
Markovic D, Pröll S and Scheer H (2007) Thermal unfolding of myoglobin: Influence of chromophore structure on stability. Biochim Biophys Acta 1767: 897–904
Marsh EN and DeGrado WF (2002) Noncovalent self-assembly of a heterotetrameric diiron protein. Proc Natl Acad Sci USA 99: 5150–5154
Masuda T, Inoue K, Masuda M, Nagayama M, Tamaki A, Ohta H, Shimada H and Takamiya K (1999) Magnesium insertion by magnesium chelatase in the biosynthesis of zinc bacteriochlorophyll a in an aerobic acidophilic bacterium Acidiphilium rubrum. J Biol Chem 274: 33594–33600
McLuskey K, Prince SM, Cogdell RJ and Isaacs NW (1999) Crystallization and preliminary X-ray crystallographic analysis of the B800-820 light-harvesting complex from Rhodopseudomonas acidophila strain 7050. Acta Cryst D Biol Cryst 55: 885–887
Meadows KA, Iida K, Tsuda K, Recchia PA, Heller BA, Antonio B, Nango M and Loach PA (1995) Enzymatic and chemical cleavage of the core light-harvesting polypeptides of photosynthetic bacteria: Determination of the minimal polypeptide size and structure required for subunit and light-harvesting complex formation. Biochemistry 35: 1559–1574
Medforth CJ, Senge MO, Smith KM, Sparks LD and Shelnutt JA (1992) Nonplanar distortion modes for highly substituted porphyrins. J Amer Chem Soc 114: 9859–9869
Mennenga A, Gärtner W, Lubitz W and Gorner H (2006) Effects of noncovalently bound quinones on the ground and triplet states of zinc chlorins in solution and bound to de novo synthesized peptides. Phys Chem Chem Phys 8: 5444–5453
Michel H, Epp O and Deisenhofer J (1986) Pigment protein interactions in the photosynthetic reaction center from Rhodopseudomonas viridis. EMBO J 5: 2445–2451
Miyake J, Kusumi T, Dudkowiad A, Goc J and Frackowiak D (1998) The interactions between bacteriochlorophyll c and amphiphilic peptides. J Photochem Photobiol A 116: 147–151
Moog RS, Kuki A, Fayer MD and Boxer SG (1984) Excitation transport and trapping in a synthetic chlorophyllide substituted hemoglobin: Orientation of the chlorophyll S1 transition dipole. Biochemistry 23: 1564–1571
Mulholland SE, Gibney BR, Rabanal F and Dutton PL (1998) Characterization of the fundamental protein ligand requirements of [4Fe-4S]2+ clusters with sixteen amino acid maquettes. J Am Chem Soc 120: 10296–10302
Mulholland SE, Gibney BR, Rabanal F and Dutton PL (1999) Determination of nonligand amino acids critical to [4Fe-4S]2+ assembly in ferredoxin maquettes. Biochemistry 38: 10442–10448
Musewald C, Hartwich G, Lossau H, Gilch P, Pöllinger-Dammer F, Scheer H and Michel-Beyerle ME (1999) Ultrafast photophysics and photochemistry of [Ni]-bacteriochlorophyll a. J Phys Chem B 103: 7055–7060
Mutter M and Vuilleumier S (1989) A chemical approach to protein design — template assembled synthetic proteins (DASP). Angew Chem Int Ed 28: 535–554
Nanda V, Rosenblatt MM, Osyczka A, Kono H, Getahun Z, Dutton PL, Saven JG and DeGrado WF (2005) De novo design of a redox-active minimal rubredoxin mimic. J Am Chem Soc 127: 5804–5805
Nango M (2006) Molecular assembly of bacteriochlorophyll complexes using synthetic light-harvesting (LH) model polypeptides. In: Grimm B, Porra R, Rüdiger W and Scheer H (eds) Chlorophylls and Bacteriochlorophylls: Biochemistry, Biophysics, Functions and Applications (Advances in Photosynthesis and Respiration, Vol 25), pp 365–373. Springer, Dordrecht
Nicholson DW and Thornberry NA (2003) Apoptosis. Life and death decisions. Science 299: 214–215
Nishimura K, Kim SG, Zhang L and Cross TA (2002) The closed state of a H+ channel helical bundle combining precise orientational and distance restraints from solid state NMR. Biochemistry 41: 13170–13177
Noguchi T, Kamimura Y, Inoue Y and Itoh S (1999) Photoconversion of awater-soluble chlorophyll protein from Chenopodium album: Resonance Raman and Fourier transform infrared study of protein and pigment structures. Plant Cell Physiol 40: 305–310
Noy D and Dutton PL (2006) Design of a minimal polypeptide unit for bacteriochlorophyll binding and self-assembly based on photosynthetic bacterial light-harvesting proteins. Biochemistry 45: 2103–2113
Noy D, Fiedor L, Hartwich G, Scheer H and Scherz A (1998) Metal-substituted bacteriochlorophylls. 2. Changes in redox potentials and electronic transition energies are dominated by intramolecular electrostatic interactions. J Am Chem Soc 120: 3684–3693
Noy D, Yerushalmi R, Brumfeld V, Ashur I, Scheer H, Baldridge KK and Scherz A (2000) Optical absorption and computational studies of [Ni]-Bacteriochlorophyll a. New insight into charge distribution between metal and ligands. J Am Chem Soc 122: 3937–3944
Noy D, Discher BM, Rubtsov IV, Hochstrasser RM and Dutton PL (2005) Design of amphiphilic protein maquettes: Enhancing maquette functionality through binding of extremely hydrophobic cofactors to lipophilic domains. Biochemistry 44: 12344–12354
Oba T and Tamiaki H (1999) Why do chlorosomal chlorophylls lack the C132-methoxycarbonyl moiety? An in vitro model study. Photosynth Res 61: 23–31
Olsen JD, Sturgis JN, Westerhuis WH, Fowler GJ, Hunter CN and Robert B (1997) Site-directed modification of the ligands to the bacteriochlorophylls of the light-harvesting LH1 and LH2 complexes of Rhodobacter sphaeroides. Biochemistry 36: 12625–32
Paulsen H (2006) Reconstitution and pigment exchange. In: Grimm B, Porra R, Rüdiger W and Scheer H (eds) Chlorophylls and Bacteriochlorophylls: Biochemistry, Biophysics, Functions and Applications (Advances in Photosynthesis and Respiration, Vol 25), pp 375–385. Springer, Dordrecht
Paulsen H and Kuttkat A (1993) Pigment complexes of light-harvesting chlorophyll a/b binding protein are stabilized by a segment in the carboxyterminal hydrophilic domain of the protein. Photochem Photobiol 57: 139–142
Pearlstein RM, Davis RC and Ditson SL (1982) Giant circular dichroism of high molecular-weight chlorophyllide-apomyoglobin complexes. Proc Natl Acad Sci USA 79: 400–402
Rabanal F, DeGrado WF and Dutton PL (1996) Toward the synthesis of a photosynthetic reaction center maquette: A cofacial porphyrin pair assembled between two subunits of a synthetic four-helix bundle multiheme protein. J Am Chem Soc 118: 473–474
Rau HK and Haehnel W (1996) Biomimetic constructs: de-novo design of redox proteins. Ber Bunsenges Phys Chem 100: 2052–2056
Rau HK and Haehnel W (1998) Design, synthesis, and properties of a novel cytochrome b model. J Am Chem Soc 120: 468–476
Rau HK, DeJonge N and Haehnel W (1998) Modular synthesis of de novo-designed metalloproteins for light-induced electron transfer. Proc Natl Acad Sci USA 95: 11526–11531
Rau HK, DeJonge N and Haehnel W (2000) Combinatorial synthesis of four-helix bundle hemoproteins for tuning of cofactor properties. Angew Chem Int Ed 39: 250–253
Rau HK, Snigula H, Struck A, Robert B, Scheer H and Haehnel W (2001) Design, synthesis and properties of synthetic chlorophyll proteins. Eur J Biochem 268: 3284–3295
Razeghifard AR and Wydrzynski T (2003) Binding of Zn-chlorin to a synthetic four-helix bundle peptide through histidine ligation. Chem Lett 42: 1024–1030
Regan L and DeGrado WF (1988) Characterization of a helical protein designed from first principles. Science 241: 976–978
Reinbothe C, Satoh H, Alcaraz J-P and Reinbothe S (2004) A novel role of water-soluble chlorophyll proteins in the transitory storage of chlorophyllide. Plant Physiol 134: 1355–1365
Robert B (1996) Resonance Raman studies in photosynthesischlorophyll and carotenoid molecules. In: Amesz J and Hoff AJ (eds) Biophysical Techniques in Photosynthesis (Advances in Photosynthesis and Respiration,Vol 3), pp 161–176. Kluwer Academic Publishers, Dordrecht
Robert B, Cogdell R and Van Grondelle R (2003) The light-harvesting system of purple bacteria. In: Green B and Parson W (eds) Light-Harvesting Antennas in Photosynthesis (Advances in Photosynthesis and Respiration, Vol 13), pp 169–194. Kluwer Academic Publishers, Dordrecht
Robertson DE, Farid RS, Moser CC, Urbauer JL, Mulholland SE, Pidikiti R, Lear JD, Wand AJ, DeGrado WF and Dutton PL (1994) Design and synthesis of multi-haem proteins. Nature 368: 425–431
Roszak AW, Howard TD, Southall J, Gardiner AT, Law CJ, Isaacs NW and Cogdell RJ (2003) Crystal structure of the RC-LH1 core complex from Rhodopseudomonas palustris. Science 302: 1969–1972
Rüdiger W (2006) Biosynthesis of chlorophylls a and b: The Last Steps. In: Grimm B, Porra R, Rüdiger W and Scheer H (eds) Chlorophylls and Bacteriochlorophylls: Biochemistry, Biophysics, Functions and Applications (Advances in Photosynthesis and Respiration, Vol 25), pp 189–200. Springer, Dordrecht
Scheer H (2003) The pigments. In: Green B and Parson W (eds) Green B and Parson W (eds) Light-Harvesting Antennas in Photosynthesis (Advances in Photosynthesis and Respiration, Vol 13), pp 29–81. Kluwer Academic Publishers, Dordrecht
Scheer H (2006) Overview. In: Grimm B, Porra R, Rüdiger W and Scheer H (eds) Chlorophylls and Bacteriochlorophylls: Biochemistry, Biophysics, Functions and Applications (Advances in Photosynthesis and Respiration, Vol 25), pp 1–26. Springer, Dordrecht
Scheer H and Hartwich G (1995) Bacterial reaction centers with modified tetrapyrrole chromophores. In: Blankenship R, Madigan MT and Bauer CE (eds) Anoxygenic Photosynthetic Bacteria (Advances in Photosynthesis and Respiration, Vol 2), pp 649–663. Kluwer Academic Publishers, Dordrecht
Scheer H and Katz JJ (1975) Nuclear magnetic resonance spectroscopy of porphyrins and metalloporphyrins. In: Smith KM (ed) Porphyrins and Metalloporphyrins, pp 399–524, Elsevier, New York
Scheer H, Paulke B and Gottstein J (1985) Long-wavelength absorbing forms of bacteriochlorophylls. II. Structural requirements for formation in Triton X-100 micelles and in aqueous methanol and acetone. In: Blauer G and Sund H (eds) Optical Properties and Structure of Tetrapyrroles, pp 507–521. De Gruyter, London
Scherz A and Parson WW (1986) Interactions of the bacteriochlorophylls in antenna bacteriochlorophyll-protein complexes of photosynthetic bacteria. Photosynth Res 9: 21–32
Scherz A, Rosenbach-Belkin V, Michalski TJ and Worcester DL (1991) Chlorophyll aggregates in aqueous solutions. In: Scheer H (ed) Chlorophylls, pp 237–268. CRC-Press, Boca Raton
Schlichter J, Friedrich J, Parbel M and Scheer H (2001) Influence of isotopic substitution on the conformational dynamics of frozen proteins. J Chem Phys 114: 9638–9644
Schmidt K, Fufezan C, Krieger-Liszkay A, Satoh H and Paulsen H (2003) Recombinant water-soluble chlorophyll protein from Brassica oleracea var. Botrys binds various chlorophyll derivatives. Biochemistry 42: 7427–7433
Schnepf R, Horth P, Bill E, Wieghardt K, Hildebrandt P and Haehnel W (2001) De novo design and characterization of copper centers in synthetic four-helix-bundle proteins. J Am Chem Soc 123: 2186–95
Schoch S and Brown J (1986) The action of chlorophyllase on chlorophyll-protein complexes. J Plant Physiol 126: 483–494
Senge MO (2000) Highly substituted porphyrins. In: Kadish KM, Smith KM, and Guilard R (eds) The Porphyrin Handbook, pp 239–347. Academic Press, San Diego
Senge MO and Smith KM (1994) Structure and conformation of photosynthetic pigments and related compounds. 7. On the conformation of the methyl ester of (20-methyl-phytochlorinato) nickel(II) — A bacteriochlorophyll c model compound. Photochem Photobiol 60: 139–142
Senge MO, Kalisch WW and Runge S (1998) Conformationally distorted chlorins via diimide reduction of nonplanar porphyrins. Tetrahedron 54: 3781–3798
Senge MO, Wiehe A and Ryppa C (2006) Synthesis, reactivity and structure of chlorophylls. In: Grimm B, Porra R, Rüdiger W and Scheer H (eds) Chlorophylls and Bacteriochlorophylls: Biochemistry, Biophysics, Functions and Applications (Advances in Photosynthesis and Respiration, Vol 25), pp 27–37. Springer, Dordrecht
Sharp RE, Diers JR, Bocian DF and Dutton PL (1998a) Differential binding of iron(III) and zinc(II) protoporphyrin IX to synthetic four-helix bundles. J Am Chem Soc 120: 7103–7104
Sharp RE, Moser CC, Rabanal F and Dutton PL (1998b) Design, synthesis, and characterization of a photoactivatable flavocytochrome molecular maquette. Proc Natl Acad Sci USA 95: 10465–10470
Shifman JM, Moser CC, Kalsbeck WA, Bocian DF and Dutton PL (1998) Functionalized de novo designed proteins: Mechanism of proton coupling to oxidation/reduction in heme protein maquettes. Biochemistry 37: 16815–16827
Shifman JM, Gibney BR, Sharp RE and Dutton PL (2000) Heme redox potential control in de novo designed four-α-helix bundle proteins. Biochemistry 39: 14813–14821
Skalicky JJ, Gibney BR, Rabanal F, Bieber Urbauer RJ, Dutton PL and Wand AJ (1999) Solution Structure of a Designed Four-α-Helix Bundle Maquette Scaffold. J Am Chem Soc 121: 4941–4951
Snigula H (2004) (Bacterio)Chlorophyll-Modifikationen zur Einlagerung in synthetische Peptide. Dissertation, Ludwig-Maximilians-Universität, München
Sparks LD, Medforth CJ, Park M-S, Chamberlain JR, Ondrias MR, Senge MO, Smith KM and Shelnutt JA (1993) Metal dependence of the nonplanar distortion of octaalkyltetra-phenylporphyrins. J Amer Chem Soc 115: 581–591
Spiedel D, Roszak AW, McKendrick K, McAuley KE, Fyfe PK, Nabedryk E, Breton J, Robert B, Cogdell RJ, Isaacs NW and Jones MR (2002) Tuning of the optical and electrochemical properties of the primary donor bacteriochlorophylls in the reaction centre from Rhodobacter sphaeroides: Spectroscopy and structure. Biochim Biophys Acta 1554: 75–93
Standfuss J, Terwisscha van Scheftinga AC, Lamborghini M and Kühlbrandt W (2005) Mechanisms of photoprotection and nonphotochemical quenching in pea light-harvesting complex at 2.5 Å resolution. EMBO J 24: 919–928
Sturgis JN, Jirsakova V, Reiss-Husson F, Cogdell RJ and Robert B (1995) Structure and properties of the bacteriochlorophyll binding site in peripheral light-harvesting complexes of purple bacteria. Biochemistry 34: 517–23
Summa CM, Rosenblatt MM, Hong JK, Lear JD and DeGrado WF (2002) Computational de novo design, and characterization of an A2B2 diiron protein. J Mol Biol 321: 923–938
Tronrud DE and Matthews BW (1993) Refinement of the structure of a water-soluble antenna complex from green photosynthetic bacteria by incorporation of the chemically determined amino acid sequence. In: Deisenhofer J and Norris JR (eds) The Photosynthetic Reaction Center, pp 13–22. Academic Press, New York
Vavilin D, Xu H, Lin S and Vermaas W (2003) Energy and electron transfer in Photosystem II of a chlorophyll b-containing Synechocystis sp. PCC 6803 mutant. Biochemistry 42: 1731–1746
Walter E, Schreiber J, Zass E and Eschenmoser A (1979) Bakteriochlorophyll a GG und Bakteriophäophytin ap in den photosynthetischen Reaktionszentren von Rhodospirillum rubrum G9. Helv Chim Acta 62: 899–920
Willner I, Heleg-Shabtai V, Katz E, Rau HK and Haehnel W (1999) Integration of a reconstituted de novo synthesized hemoprotein and native metalloproteins with electrode supports for bioelectronic and bioelectrocatalytic applications. J Am Chem Soc 121: 6455–6468
Woodward RB, Ayer WA, Beaton JM, Bickelhaupt F, Bonnett R, Buchschacher P, Closs GL, Dutler H, Hannah J, Hauck FP, Ito S, Langemann A, LeGoff E, Leimgruber W, Lwowski W, Sauer J, Valenta Z and Voltz H (1960) The total synthesis of chlorophyll. J Amer Chem Soc 82: 3800–3802
Wright KA and Boxer SG (1981) Solution properties and synthetic chlorophyllide-apomyoglobin and bacteriochlorophyllide-apomyoglobin complexes. Biochemistry 20: 7546–7556
Yeates TO, Komiya H, Chirino A, Rees DC, Allen JP and Feher G (1988) Structure of the reaction center from Rhodobacter sphaeroides R-26 and 2.4.1 : Protein-cofactor (bacteriochlorophyll, bacteriopheophytin and carotenoid) interactions. Proc Natl Acad Sci USA 85: 7993–7997
Yerushalmi R, Ashur I and Scherz A (2006) Metal-substituted bacteriochlorophylls: novel molecular tools. In: Grimm B, Porra R, Rüdiger W and Scheer H (eds) Chlorophylls and Bacteriochlorophylls: Biochemistry, Biophysics, Functions and Applications (Advances in Photosynthesis and Respiration, Vol 25), pp 495–506. Springer, Dordrecht
Zhang Z, Huang L, Shulmeister VM, Chi Y-I, Kim KK, Hung L-W, Crofts AR, Berry EA and Kim S-H (1998) Electron transfer by domain movement in cytochrome bc 1 Nature 392: 677–684
Zouni A, Witt HT, Kern J, Fromme P, Krauss N, Saenger W and Orth P (2001) Crystal structure of Photosystem II from Synechococcus elongatus at 3.8 Å resolution. Nature 409: 739–743
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Haehnel, W., Noy, D., Scheer, H. (2009). De novo Designed Bacteriochlorophyll-Binding Helix-Bundle Proteins. In: Hunter, C.N., Daldal, F., Thurnauer, M.C., Beatty, J.T. (eds) The Purple Phototrophic Bacteria. Advances in Photosynthesis and Respiration, vol 28. Springer, Dordrecht. https://doi.org/10.1007/978-1-4020-8815-5_45
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