Abstract
The binding of proteins to individual glycoconjugates is often weak. In physiological settings, carbohydrate–protein interactions often benefit from multivalency—multiple copies of the carbohydrate epitope engage with multiple copies of a carbohydrate–binding protein. This mode of molecular recognition is especially important in cell adhesion because the individual interactions need to be kinetically labile yet highly specific. This review discusses why protein–carbohydrate interactions are especially well-suited for multivalent binding, the binding modes and energetic forces that underlie multivalent protein–carbohydrate complexes, and the utility of multivalent carbohydrate derivatives for exploring multivalent binding and inhibiting physiologically and medically important protein–carbohydrate interactions.
Similar content being viewed by others
Abbreviations
- ASGR:
-
asialoglycoprotein receptor
- ATRP:
-
atom-transfer radical polymerization
- bFGF:
-
basic fibroblast growth factor
- BSA:
-
bovine serum albumin
- ConA:
-
concanavalin A
- ELLA:
-
enzyme-linked lectin inhibition assay
- EcorL:
-
Erythrina corallodendrum
- FRET:
-
Förster resonance energy transfer
- LOL I:
-
Lathyrus ochrus lectin I
- LT:
-
labile enterotoxin
- LFA:
-
Limax flavus
- MBPs:
-
mannose-binding proteins
- PAMAM:
-
polyamidoamine
- ROMP:
-
ring-opening metathesis polymerization
- SLT:
-
Shiga-like toxins
- SPR:
-
surface plasmon resonance
References
Varki A (1993) Glycobiology 3:97
Sharon N (2007) J Biol Chem 282:2753
Gabius HJ (2006) Crit Rev Immunol 26:43
Nilsson CL (2003) Anal Chem 75:348A
Bertozzi CR, Kiessling LL (2001) Science 291:2357
Weis WI, Drickamer K (1996) Annu Rev Biochem 65:441
Zelensky AN, Gready JE (2005) FEBS J 272:6179
Barre A, Bourne Y, Van Damme EJ, Peumans WJ, Rouge P (2001) Biochimie 83:645
Rini JM (1995) Annu Rev Biophys Biomol Struct 24:551
Quiocho FA (1989) Pure Appl Chem 61:1293
Williams BA, Chervenak MC, Toone EJ (1992) J Biol Chem 267:22907
Liao D-I, Kapadia G, Ahmed H, Vasta GR, Herzberg O (1994) Proc Natl Acad Sci USA 91:1428
Loris R, Stas PPG, Wyns L (1994) J Biol Chem 269:26722
Lemieux RU (1996) Acc Chem Res 29:373
Quiocho RA, Wilson DK, Vyas NK (1989) Nature 340:404
Burley SKP (1985) Science 229:23
Butterfield SM, Sweeney MM, Waters ML (2005) J Org Chem 70:1105
Lis H, Sharon N (1986) Annu Rev Biochem 55:35
Borrok MJ, Kiessling LL (2007) J Am Chem Soc 129:12780
Borrok MJ, Kiessling LL, Forest KT (2007) Protein Sci 16:1032
Lemieux RU, Pavia AA, Martin JC, Watanabe KA (1969) Can J Chem 47:4427
Somers WS, Tang J, Shaw GD, Camphausen RT (2000) Cell 103:467
Feinberg H, Mitchell DA, Drickamer K, Weis WI (2001) Science 294:2163
Weis WI, Kahn R, Fourme R, Drickamer K, Hendrickson WA (1991) Science 254:1608
Forseen SKK (1994) Calcium in biological systems. In: Bertini IG, Lippard HB, Valentine JS (eds) Bioinorganic Chemistry. University Science Books, Mill Valley, pp 107–166
Faham S, Hileman RE, Fromm JR, Linhardt RJ, Rees DC (1996) Science 271:1116
DiGabriele AD, Lax I, Chen DI, Svahn CM, Jaye M, Schlessinger J, Hendrickson WA (1998) Nature 393:812
Pellegrini L, Burke DF, von Delft F, Mulloy B, Blundell TL (2000) Nature 407:1029
Pellegrini L (2001) Curr Opin Struct Biol 11:629
Mohammadi M, Olsen SK, Goetz R (2005) Curr Opin Struct Biol 15:506
Bourne Y, Rouge P, Cambillau C (1990) J Biol Chem 265:18161
Chervenak MC, Toone EJ (1994) J Am Chem Soc 116:10533
Chervenak MC, Toone EJ (1995) Biochemistry 34:5685
Clarke C, Woods RJ, Gluska J, Cooper A, Nutley MA, Boons GJ (2001) J Am Chem Soc 123:12238
Li Z, Lazardis T (2005) J Phys Chem B 109:662
Casu B, Petitou M, Provasoli M, Sinay P (1988) TIBS 13:221
Xu QW, Bush CA (1996) Glycobiology 6:1704
Woods RJ (1995) Curr Opin Struct Biol 5:591
Carver JP (1993) Pure Appl Chem 65:763
Bundle DR, Alibes R, Nilar S, Otter A, Warwas M, Zhang P (1998) J Am Chem Soc 120:5317
Lindh I, Hindsgaul O (1991) J Am Chem Soc 113:216
Praly J-P, Lemieux RU (1987) Can J Chem 65:213
Johnson GP, Stevens ED, French AD (2007) Carbohydr Res 342:1210
Kurutz JK, Kiessling LL (1997) Glycobiology 7:337
Lee YC, Lee RT (1995) Acc Chem Res 28:321
Kiessling LL, Pohl NL (1996) Chem Biol 3:71
Roy R (1996) Curr Opin Struct Biol 6:692
Mammen M, Choi SK, Whitesides GM (1998) Angew Chem Int Edit Eng 37:2754
Kitov PI, Bundle DR (2003) J Am Chem Soc 125:16271
Lundquist JJ, Toone EJ (2002) Chem Rev 102:555
Wolfenden ML, Cloninger MJ (2005) J Am Chem Soc 127:12168
Jencks WP (1981) Proc Natl Acad Sci USA 78:4046
Page MI, Jencks WP (1971) Proc Natl Acad Sci USA 68:1678
Cairo CW, Gestwicki JE, Kanai M, Kiessling LL (2002) J Am Chem Soc 124:1615
Gestwicki JE, Cairo CW, Strong LE, Oetjen KA, Kiessling LL (2002) J Am Chem Soc 124:14922
Kiessling LL, Strong LE, Gestwicki JE (2000) Annu Rep Med Chem 35:321
Crothers DM, Metzger H (1972) Immunochemistry 9:341
Rao JH, Lahiri J, Isaacs L, Weis RM, Whitesides GM (1998) Science 280:708
Kiessling LL, Gestwicki JE, Strong LE (2006) Angew Chem-Int Edit 45:2348
Pohl NL, Kiessling LL (1999) Synthesis SI:1515
Wright CS (1984) J Mol Biol 178:91
Hester G, Kaky H, Goldstein IJ, Wright CS (1995) Nat Struct Biol 2:472
Anderson CF, Record MT (1990) Annu Rev Biophys Biophys Chem 19:423
Mortell KH, Weatherman RV, Kiessling LL (1996) J Am Chem Soc 118:2297
Lee RT, Lee YC (1987) Glycoconjugate J 4:317
Carlson CB, Mowery P, Owen RM, Dykhuizen EC, Kiessling LL (2007) ACS Chem Biol 2:119
Alon R, Hammer DA, Springer TA (1995) Nature 374:539
Ashwell G, Harford J (1982) Ann Rev Biochem 51:531
Lodish HF (1991) TIBS 16:374
Connolly DT, Townsend RR, Kawaguchi K, Bell WR, Lee YC (1982) J Biol Chem 257:939
Lee YC, Townsend RR, Hardy MR, Lönngren J, Arnarp J, Haraldsson M, Lönn H (1983) J Biol Chem 258:199
Baenziger JU, Maynard Y (1980) J Biol Chem 255:4607
Spiess M (1990) Biochemistry 29:10009
Ikeda K, Sannoh T, Kawasaki N, Kawasaki T, Yamashina I (1987) J Biol Chem 262:7451
Weis WI (1994) Structure 2:147
Fan E, Merritt EA, Verlinde CLMJ, Hol WGJ (2000) Curr Opin Struct Biol 10:680
Karmali MA, Petric M, Lim C, Fleming PC, Arbus GS, Lior H (1985) J Infect Dis 151:775
Ling H, Boodhoo A, Hazes B, Cummings MD, Armstrong GD, Brunton JL, Read RJ (1998) Biochemistry 37:1777
Kitov PI, Sadowska JM, Mulvey G, Armstrong GD, Ling H, Pannu NS, Read RJ, Bundle DR (2000) Nature 403:669
Burke SD, Zhao Q, Schuster MC, Kiessling LL (2000) J Am Chem Soc 122:4518
Gestwicki JE, Strong LE, Cairo CW, Boehm FJ, Kiessling LL (2002) Chem Biol 9:163
Fan EK, Zhang ZS, Minke WE, Hou Z, Verlinde C, Hol WGJ (2000) J Am Chem Soc 122:2663
Zhang Z, Merritt EA, Ahn M, Roach C, Hou Z, Verlinde CL, Hol WG, Fan EK (2002) J Am Chem Soc 124:12991
Merritt EA, Zhang Z, Pickens JC, Ahn M, Hol WG, Fan EK (2002) J Am Chem Soc 124:8818
Pukin AV, Branderhorst HM, Sisu C, Weijers CA, Gilbert M, Liskamp RM, Visser GM, Zuilhof H, Pieters RJ (2007) ChemBioChem 8:1500
Polizzotti BD, Maheshwari R, Vinkenborg J, Kiick KL (2007) Macromolecules 40:7103
Bevilacqua MP, Stengelin S, Gimbrone MA, Seed B (1989) Science 243:1160
Lasky LA (1995) Annu Rev Biochem 64:113
Luster AD, Alon R, von Andrian UH (2005) Nat Immunol 6:1182
Ley K (2003) Trends Mol Med 9:263
Gonzalez-Amaro R, Sanchez-Madrid F (1999) Crit Rev Immunol 19:389
Simanek EE, McGarvey GJ, Jablonowski JA, Wong C-H (1998) Chem Rev 98:833
Kaila N, Thomas BE (2003) Exp Opin Therap Patents 13:305
DeFrees SA, Kosch W, Way W, Paulson JC, Sabesan S, Halcomb RL, Huang DH, Ichikawa Y, Wong C-H (1995) J Am Chem Soc 117:66
Miyauchi H, Yuri M, Tanaka M, Kawamura N, Hayashi M (1997) Bioorg Med Chem Lett 7:989
Rosen SD, Bertozzi CR (1994) Curr Opin Cell Biol 6:663
Weatherman RV, Mortell KH, Chervenak M, Kiessling LL, Toone EJ (1996) Biochemistry 35:3619
Dimick SM, Powell SC, McMahon SA, Moothoo DN, Naismith JH, Toone EJ (1999) J Am Chem Soc 121:10286
Aoi K, Itoh K, Okada M (1995) Macromolecules 28:5391
Smith DK, Diederich F (1998) Chem-Eur J 4:1353
Seebach D, Abele S, Gademann K, Guichard G, Hintermann T, Juan B, L. MJ, Schreiber JV (1998) Helv Chim Acta 81:932
Kim Y, Zimmerman SC (1998) Curr Opin Chem Biol 2:733
Fréchet JM (1994) Science 263:1710
Cloninger MJ (2002) Curr Opin Chem Biol 6:742
Dubber M, Lindhorst TK (1998) J Chem Soc Chem Commun 1265:
Ashton PR, Hounsell EF, Jayaraman N, Nilsen TM, Spencer N, Stoddart JF, Young M (1998) J Org Chem 63:3429
Lindhorst TK, in Host-Guest Chemistry. (2002), vol. 218, pp 201
Wolfenden ML, Cloninger MJ (2006) Bioconj Chem 17:958
Roy R, Zanini D, Meunier SJ, Romanowska A (1993) J Chem Soc, Chem Commun 1869
Reuter JD, Myc A, Hayes MM, Gan Z, Roy R, Qin D, Yin R, Piehler LT, Esfand R, Tomalia DA, Baker JR Jr (1999) Bioconjugate Chem 10:271
Vrasidas I, Andre S, Valentini P, Bock C, Lensch M, Kaltner H, Liskamp RMJ, Gabius HJ, Pieters RJ (2003) Org Biomol Chem 1:803
Yamazaki N, Kojima S, Gabius S, Gabius H (1992) Int J Biochem 24:99
Matsuo H, Funato K, Harashima H, Kiwada H (1994) J Drug Targeting 2:141
Kingery-Wood JE, Williams KW, Sigal GB, M. WG (1992) J Am Chem Soc 114:7303
Spevak W, Nagy JO, Charych DH, Schaefer ME, Gilbert JH, Bednarski MD (1993) J Am Chem Soc 115:1146
DeFrees SA, Phillips L, Guo L, Zalipsky S (1996) J Am Chem Soc 118:6101
Spevak W, Foxall C, Charych DH, Dasgupta F, Nagy JO (1996) J Med Chem 39:1018
Preobrazhenskaya ME, Berman AE, Mikhailov VI, Ushakova NA, Mazurov AV, Semenov AV, Usov AI, Nifant'ev NE, Bovin NV (1997) Biochem Mol Bio Int 43:443
Larsen GR, Sako D, Ahern TJ, Shaffer M, Erban J, Sajer SA, Gibson RM, Wagner DD, Furie BC, Furie B (1992) J Biol Chem 267:11104
Liu W-J, Ramachandran V, Kang J, Kishimoto TK, Cummings RD, McEver RP (1998) J Biol Chem 273:7078
Manning DD, Hu X, Beck PJ, Kiessling LL (1997) J Am Chem Soc 119:3161
Sako D, Comess KM, Barone KM, Camphausen RT, Cumming DA, Shaw GD (1995) Cell 83:323
Pouyani T, Seed B (1995) Cell 63:333
Guo C-T, Sun X-L, Kanie O, Shortridge KF, Suzuki T, Miyamoto D, Hidari K, Wong C-H, Suzuki Y (2002) Glycobiology 12:183
Liang R, Loebach J, Horan N, Ge M, Thompson C, Yan L, Kahne D (1997) Proc Natl Acad Sci USA 94:10554
Liang R, Yan L, Loebach J, Ge M, Uozumi Y, Sekanina K, Horan N, Gildersleeve J, Thompson C, Smith A, Biswas K, Still WC, Kahne D (1996) Science 274:1520
Rheinnecker M, Hardt C, Ilag LL, Kufer P, Gruber R, Hoess A, Lupas A, Rottenberger C, Plückthun A, P. P (1996) J Immunol 157:2989
Love KR, Seeberger PH (2002) Angew Chem-Int Edit 41:3583
Timmer MSM, Stocker BL, Seeberger PH (2007) Curr Opin Chem Biol 11:59
Stevens J, Blixt O, Paulson JC, Wilson IA (2006) Nat Rev Microbiol 4:857
Turnbull JE, Linhardt RJ (2006) Nat Chem Biol 2:449
Paulson JC, Blixt O, Collins BE (2006) Nat Chem Biol 2:238
Fukui S, Feizi T, Galustian C, Lawson AM, Chai WG (2002) Nat Biotechnol 20:1011
Smith EA, Thomas WD, Kiessling LL, Corn RM (2003) J Am Chem Soc 125:6140
Kiessling LL, Cairo CW (2002) Nat Biotechnol 20:234
Weply J, Abbes S, Scudder P, Keene J, Broschel K, Casnocha S, Gorka C, Steinenger C, Howard S, Schmuke J, Granelo M, Roissert J, Manger I, Jacob G (1994) Glycobiology 4:256
Horejsi V, Smolek P, Kocourek J (1978) Biochim Biophys Acta 538:293
Kallin E (1994) Methods Enzymol 242:221
Kobayashi K, Akaike T, Usui T (1994) Methods Enzymol 242:226
Nishimura S, Furuike T, Matsuoka K (1994) Methods Enzymol 242:235
Roy R (1996) Trends Glycosci Glycotechnol 8:79
Bovin NV, Gabius H-J (1995) Chem Soc Rev 24:413
Bovin NV, Korchagina EY, Zemlyanukhina TV, Byramova NE, Galanina OE, Zemlyakov AE, Ivanov AE, Zubov VP, Mochalova LV (1993) Glycoconjugate J 10:142
Miyauchi H, Tanaka M, Koike H, Kawamura N, Hayashi M (1997) Bioorg Med Chem Lett 7:985
Spaltenstein A, Whitesides GM (1991) J Am Chem Soc 113:686
Gamian A, Chomik M, Laferriere CA, Roy R (1991) Can J Microbiol 37:233
Matrosovich MN, Mochalova LS, Marinina VP, Byramova NE, Bovin NV (1990) FEBS Lett 272:209
Roy R, Tropper F (1988) J Chem Soc Chem Commun 1058:
Mammen M, Dahmann G, Whitesides GM (1995) J Med Chem 38:4179
Roy R, Park WKC, Srivastava OP, Foxall C (1996) Biorg Med Chem Lett 6:1399
Fan J-Q, Quesenberry MS, Takegawa K, Iwahara S, Kondo A, Kato I, Lee YC (1995) J Biol Chem 270:17730
Nishimura SI, Kee KB, Matsuoka K, Lee YC (1994) Biochem Biophys Res Commun 199:249
Ohno K, Tsujii Y, Miyamoto T, Fukuda T, Goto M, Kobayashi K, Akaike T (1998) Macromolecules 31:1064
Hawker CJ (1998) Acc Chem Res 30:373
Matyjaszewski K, Xia JH (2001) Chem Rev 101:2921
Griffith BR, Allen BL, Rapraeger AC, Kiessling LL (2004) J Am Chem Soc 126:1608
Spain SG, Gibson MI, Cameron NR (2007) J Polym Sci Pol Chem 45:2059
Narain R (2006) React Funct Polym 66:1589
Vazquez-Dorbatt V, Maynard HD (2006) Biomacromolecules 7:2297
Muthukrishnan S, Zhang MF, Burkhardt M, Drechsler M, Mori H, Muller AHE (2005) Macromolecules 38:7926
Sen Gupta S, Raja KS, Kaltgrad E, Strable E, Finn MG (2005) Chem Commun 4315
Sigal GB, Mammen M, Dahmann G, Whitesides GM (1996) J Am Chem Soc 118:3789
Choi S-K, Mammen M, Whitesides GM (1996) Chem Biol 3:97
Thoma G, Magnani JL, Ohrlein R, Ernst B, Schwarzenbach F, Duthaler RO (1997) J Am Chem Soc 119:7414
Thoma G, Ernst B, Schwarzenbach F, Duthaler RO (1997) Bioorg Med Chem Lett 7:1705
Ali M, Hicks AE, Hellewell PG, Thoma G, Norman KE (2004) FASEB J 18:152
Thoma G, Duthaler RO, Magnani JL, Patton JT (2001) J Am Chem Soc 123:10113
Imai Y, Matsuura Y, Ono Y, Ishikawa T, Ito Y (2001) J Biochem (Tokyo) 130:665
Kamitakahara H, Suzuki T, Nishigori N, Suzuki Y, Kanie O, Wong C-H (1999) Angew Chem Int Ed Eng 37:1524
Nomura K, Schrock RR (1996) Macromolecules 29:540
Mortell KH, Gingras M, Kiessling LL (1994) J Am Chem Soc 116:10253
Fraser C, Grubbs RH (1995) Macromolecules 28:7248
Sanders WJ, Gordon EJ, Beck PJ, Alon R, Kiessling LL (1999) J Biol Chem 274:5271
Lynn DM, Kanaoka S, Grubbs RH (1996) J Am Chem Soc 118:784
Trnka TM, Grubbs RH (2001) Acc Chem Res 34:18
Sampson NS, Lee Y (2006) Curr Opin Struct Biol 16:544
Kiessling LL, Gestwicki JE, Strong LE (2000) Curr Opin Chem Biol 4:696
Weatherman RV, Kiessling LL (1996) J Org Chem 61:534
Dias EL, Nguyen ST, Grubbs RH (1997) J Am Chem Soc 119:3887
Kanai M, Mortell KH, Kiessling LL (1997) J Am Chem Soc 119:9931
Mann DA, Kanai M, Maly DJ, Kiessling LL (1998) J Am Chem Soc 120:10575
Kansas GS (1996) Blood 88:3259
McEver RP, Moore KL, Cummings RD (1995) J Biol Chem 270:11025
Tedder TF, Steeber DA, Chen A, Engel P (1995) FASEB J 9:866
Rosen SD, Bertozzi CR (1996) Curr Biol 6:261
Varki A (1994) Proc Natl Acad Sci USA 91:7390
Hemmerich S, Leffler H, Rosen SD (1995) J Biol Chem 270:12035
Wilkins PP, McEver RP, Cummings RD (1996) J Biol Chem 271:18732
Shailubhai K, Streeter PR, Smith EE, Jacob GS (1997) Glycobiology 7:305
Moore KL, Eaton SF, Lyons DE, Lichenstein HS, Cummings RD, McEver RP (1994) J Biol Chem 269:23318
Hemmerich S, Rosen SD (1994) Biochemistry 33:4830
Hemmerich S, Bertozzi CR, Leffler H, Rosen SD (1994) Biochemistry 33:4820
Uchimura K, Rosen SD (2006) Trends Immunol 27:559
Uchimura K, Gauguet JM, Singer MS, Tsay D, Kannagi R, Muramatsu T, von Andrian UH, Rosen SD (2005) Nat Immunol 6:1105
Sanders WJ, Katsumoto TR, Bertozzi CR, Rosen SD, Kiessling LL (1996) Biochemistry 35:14862
Yuen C-T, Lawson AM, Chai W, Larkin M, Stoll MS, Stuart AC, Sullivan FX, Ahern TJ, Feizi T (1992) Biochemistry 31:9126
Galustian C, Lawson AM, Komba S, Ishida H, Kiso M, Feizi T (1998) Biochem Biophys Res Commun 240:748
Mitsuoka C, Kasugai-Sawada M, Ando-Furui K, Izawa M, Nakanishi H, Nakamura S, Ishida H, Kiso M, Kannagi R (1998) J Biol Chem 273:11225
Gordon EJ, Sanders WJ, Kiessling LL (1998) Nature 392:30
Green PJ, Tamatani T, Watanabe T, Miyasaka M, Hasegawa A, Kiso M, Yuen C-T, Stoll MS, Feizi T (1992) Biochem Biophys Res Commun 188:244
Green PJ, Yuen C-T, Childs RA, CHai W, Miyasaka M, Lemoine R, Lubineau A, Smith B, Ueno H, Nicolaou KC, Feizi T (1995) Glycobiology 5:29
Scudder PR, Shailubhai D, Duffin KL, Streeter PR, Jacob GS (1994) Glycobiology 4:929
Crottet P, Kim YJ, Varki A (1996) Glycobiology 6:191
Finger EB, Puri KD, Alon R, Lawrence MG, von Andrian UH, Springer TA (1996) Nature 379:266
Mowery P, Yang ZQ, Gordon EJ, Dwir O, Spencer AG, Alon R, Kiessling LL (2004) Chem Biol 11:725
Strong LE, Kiessling LL (1999) J Am Chem Soc 121:6193
Gordon EJ, Gestwicki JE, Strong LE, Kiessling LL (2000) Chem Biol 7:9
Owen RM, Gestwicki JE, Young T, Kiessling LL (2002) Org Lett 4:2293
Roberts KS, Sampson NS (2004) Org Lett 6:3253
Yang ZQ, Puffer EB, Pontrello JK, Kiessling LL (2002) Carbohydr Res 337:1605
Charych D, Cheng Q, Reichert A, Kuziemko G, Stroh M, Nagy JO, Spevak W, Stevens RC (1996) Chem Biol 3:113
Gonsho A, Irie K, Susaki H, Iwasawa H, Okuno S, Sugawara T (1994) Biol Pharm Bull 17:275
Merwin JR, Noell GS, Thomas WL, Chiou HC, Derome ME, McKee TD, Spitalny GL, Findeis MA (1994) Bioconj Chem 5:612
Crocker PR, Feizi T (1996) Curr Opin Struct Biol 6:679
Lind SS, Parker W, Everett ML, Platt JL (1998) Glycobiology 8:433
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2008 Springer-Verlag Berlin Heidelberg New York
About this entry
Cite this entry
Kiessling, L., Young, T., Gruber, T., Mortell, K. (2008). Multivalency in Protein–Carbohydrate Recognition. In: Fraser-Reid, B.O., Tatsuta, K., Thiem, J. (eds) Glycoscience. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-30429-6_64
Download citation
DOI: https://doi.org/10.1007/978-3-540-30429-6_64
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-540-36154-1
Online ISBN: 978-3-540-30429-6
eBook Packages: Chemistry and Materials ScienceReference Module Physical and Materials ScienceReference Module Chemistry, Materials and Physics