Abstract
The concept of using a molecular template to generate recognition sites for selective separations or reactions within a polymeric network is an exciting, challenging and far-reaching one. This review seeks to explain and define the concept and its components. It traces the early developments by the pioneers in the field and highlights the important advances made, or the key crossroads passed, in reaching the current state-of-the-art. The various types of templates and template binding which have been explored are reviewed and achievements in re-binding or recognition discussed. Finally, the practicalities of preparing polymer networks imprinted in this manner are dealt with and guidance given in what is currently achievable and what limitations still exist.
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15 References
Wulff G (1986) ACS Symp Ser 308: 186–130 In: Ford WT (ed) Polymeric reagnets and catalysts. Molecular recognition in polymers prepared by imprinting with templates. Washington DC
Watson JD, Crick FHC (1953) Nature (Lon) 171: 737
Todd AR (1956) In: Todd AR Perspectives in organic chemistry. Interscience, London, p 263
Vlatakis G, Andersson LI, Mueller R, Mosbach K (1993). Nature 361: 645–7
Mutter M (1989) Angew Chim Int Edn 28: 535
Mutter M, Tuchscherver GG, Miller GG, Altmann KH, Carey RI, Wyss DS, Labhard AM and Rivier TE (1992) J Amer Chem Soc 114: 1463
Mutter M and Tuchscherver GG (1988) Die Makromol. Chem Rapid 9: 437
Schultz PG (1988) Science 240: 426
Atherton E and Shepherd RC (1989) Solid Phase Peptide Synthesis, Oxford University Press
Lerner R, Benkovics SJ and Schultz PG (1991) Science 252: 659
Schultz DG and Lerner RA (1993) Acc Chem Res 26: 391
Lehn JM, Rigault A, Siegel J, Harrowfield J, Chevrier B and Mobras D (1987) Proc Natal Acad Sci USA 84: 2565
Lehn JM and Rigault A (1988) Angew Chem Intl. Edn 27: 1095.
Dietrich-Buchecker C and Sauvage JP (1992) New J Chem 16: 277
Dietrich-Buchecker C and Sauvage JP (1992) Bull Soc Chim Fr 129: 113
Anelli PL, Delgado M, Gandolfi MT, Goodnov TT, Kaifer AE, Philp D, Pietrazkiewiz M, Prodi L, Reddington MV, Slawin AMZ, Spencer N, Stoddart JF, Vincent C and Williams DJ (1992) J Amer Chem Soc 114: 193
Sauwage JP (1993) Ed New J Chem 17: pp 619–763
Gokel GW and Korzeniowski SH (1982) Macrocylic Polyether Syntheses, Springer Verlag, Berlin
Anderson S, Anderson HL and Saunders JKM (1993) Acc Chem Res 26: 469
Busch DH (1992) J Incl Phenom Mol Recog 12: 389–395
Busch DH and Stevenson NA (1990) Coord Chem Rev 100: 119–54
Lindsey JS (1991) New J Chem 15: 153–180
Broer DJ and Heynderickx I (1990) Macromols 23: 2474–77
Percec V, Heck J, Johansson G and Ungar G (1993) Polym Prepr March, 116–7
Challa G and Tan YY (1981) Pure Appl Chem 53: 627
Shavit N and Cohen J (1977) Polymerisation in Organised Systems, ed Elias HG, Gordon and Breach, London p 213
Wulff G and Sarhan A (1972) Angew Chem Int Ed Engl 84: 364–5
Wulff G, Sarhan A and Sabrocki K (1973) Tetrahedron Lett 37: 4329–32
Dunkin IR, Sherrington DC and Steinke J (1994) unpublished results. Steinke J Ph.D. Thesis University of Strathclyde, Glasgow, U.K.
Guyot A (1988) In: Syntheses and Separations Using Functional Polymers, Sherrington DC and Hodge P Eds J Wiley and Sons, Chichester, U.K. Chap. 1. p1.
Mudd S (1932) J Immunol 23: 423–7
Pauling L (1940) J Amer Chem Soc 62: 2643–57
Pressman D and Pauling L (1949) J Amer Chem Soc 71: 2893–2899
Dickey FH (1949) Proc Natl Acad Sci 35: 277–9
Dickey FH (1955) J Phys Chem 59: 695–707
Bernhard SA (1952) J Amer Chem Soc 74: 4946–7
Erlenmeyer H and Bartels H (1964) Helv Chim Acta 47: 46–51
Haldeman RG and Emmett PH (1955) J Phys Chem 59: 1039–43
Curti R, Colombo U and Clerici F (1952) Gazz Chim Ital 82: 491–502
Morrison JL, Worsley M, Shaw DR and Hodgson GW (1959) Can J Chem 37: 1986–95
Bartels H and Prijs B (1974) Adv Chrom 11: 115–43
Bartels H (1967) J Chrom 30: 113–6
Curti R and Colombo U (1952) J Amer Chem Soc 74: 3961
Beckett AH (1957) Nature 179: 1074
Beckett AH and Anderson P (1960) J Pharm Pharmacol 12: 228T–36T
Beckett AH and Youssef HZ (1963) J Pharm Pharmacol 15: 253T–66T
Erlenmeyer H and Bartels H (1964) Helv Chem Acta 47: 1285–88
Bartels H and Erlenmeyer H (1965) Helv Chim Acta 48: 285–90
Erlenmeyer H and Bartels H (1965) Helv Chim Acta 48: 301–3
Bartels H, Prijs B and Erlenmeyer H (1966) Helv Chim Acta 49: 621–25
Bartels H (1967) Z Anorg Allg Chem 350: 143–7
Kaiser GG and Andersson JT (1992) Fres J Analyt Chem 342: 834–9
Takagishi T and Klotz IM (1972) Biopolymers 11: 483–91
Takagishi T, Hayashi A and Kuroki N. (1982) J Polym Sci Polym Chem Ed 20: 1533–47
Takagishi T, Sugimoto T, Hamano H, Lim Y.-J., Kuroki N and Kuzoka H (1984) J Polym Sci Polym Lett Ed 22: 283–9
Takagishi T, Sugimoto T. Hamano H, Lim Y.-J. and Kuroki N (1984) J Polym Sci Polym Chem Ed (1984) 22: 4035–9
Takagishi T, Hamana H, Shimokado T and Kuroki N (1985) J Polym Sci Polym Lett Ed (1985) 23: 545–8
Kozuka H, Takagishi T, Yoshikawa K, Kuroki N and Mitsuishi M (1985) J Polym Sci Polym Chem Ed (1985) 24: 2695–700
Takagishi T and Okada M (1986) Chem Express 1: 359–62
Shinkai S, Yamada M, Sone T and Manabe O (1983) Tetrahedron Lett 24: 3501–4
Cleland WW (1975) Acc Chem Res 8: 145–51
Wulff G (1993) Makromol Chem Macromol Symp 70: 285–8
Wulff G, Minarik M and Schauhoff S (1991) GIT Fachz Lab 35: 10–12, 15–17
Wulff G and Haarer J (1991) Makromol Chem 192: 1329–38
Damen J and Neckers DC (1980) J Amer Chem Soc 102: 3265–7
Damen J and Neckers DC (1980) J Org Chem 45: 1382–7
Sarhan A (1982) Makromol Chem Rapid Commun 3: 489–94
Sarhan A, Ali MM and Abdelaal MY (1989) React Polym 11: 57–70
Sarhan A (1989) Makromol Chem 190: 2031–9
Shea KJ and Thompson EA (1978) J Org Chem 43: 4253–5
Wulff G and Minarik M. (1990) J Liq Chrom 13: 2987–3001
Wulff G, Poll H.-G, Minarik M (1986) J Liq Chrom 9: 385–405
Steinke JHG (1990) Diplomarbeit, Heinrich-Heine-Universität Düsseldorf
Wulff G, Vietmeier J and Poll H-G (1987) Makromol Chem 188: 731–40
Wulff G and Vesper W (1978) J Chrom 167: 171–86
Wulff G, Oberkobusch D and Minarik M (1985) React Polym 3: 161–75
Wulff G, Vesper W, Grobe-Einsler R and Sarhan A (1977) Makromol Chem 178: 2817–25
Sarhan A and Wulff G (1982) Macromol Chem 183: 85–92.
Wulff G and Sarhan A (1982) Makromol Chem 183: 1603–1614
Wulff G and Sarhan A (1982) Makromol Chem 188: 741–48
Wulff G, Best W and Akelah A (1984) React Polym Exch Sorb 2: 167–74
Damen J and Neckers DC (1980) Tetrahedron Lett 21: 1913–6
Shea KJ and Sasaki DY (1989) J Amer Chem Soc 111: 3442–4
Shea KJ and Dougherty TK (1986) J Amer Chem Soc 108: 1091.3
Wulff G (1982) Pure Appl Chem 54: 2039–102
Wulff G, Schultze I, Zabrocki K and Vesper W (1980) Makromol Chem 181: 531–44
Wulff G, Vesper W, Grobe-Einsler R and Sarham A (1977) Makromol Chem 178: 2799–816
Wulff G and Vietmeier J (1989) Makromol Chem 190: 1717–26
Wulff G and Vietmeier J (1989) Makromol Chem 190: 1727–35
Sellergren B, Lepistö M and Mosbach K (1988) J Amer Chem Soc 110: 5853–60
Arshady R and Mosbach K (1981) Makromol Chem 182: 687–92
Andersson LI, Miyabayashi A, O'Shannessy DJ and Mosbach K (1990) J Chrom 516: 323–33
Ekberg B and Mosbach K (1989) TIBTECH 7: 92–6
Fischer L, Mueller R, Ekberg B and Mosbach K (1991) J Amer Chem Soc 113: 9358–60
Lepistö M and Sellergren B (1989) J Org Chem 54: 6010–2
Sellergren B (1989) Makromol Chem 190: 2703–11
Sellergren B and Andersson LI (1990) J Org Chem 55: 3381–2
Sellergen B (1989) Chirality 1: 63–8
Andersson LI (1988) React Polym 9: 29–41
Andersson LI and Mosbach K (1990) J Chrom 516: 313–23
Andersson LI, Sellergren B and Mosbach K (1984) Tetrahedron Lett 25: 5211–14
Andersson LI and Mosbach K (1990) J Chrom 516: 313–23
Sellergren B and Nilsson KGI (1989) Meth Mol Cell Biol 1: 59–62
Anderson LI, O'Shannessy DJ and Mosbach K (1990) J Chrom 513: 167–81
O'Shannessy DJ, Ekberg B and Mosbach K (1989) Anal Biochem 177: 144–51
Sellergren B and Shea KJ (1993) J Chrom 635: 31–49
Sellergren B, Ekberg B and Mosbach K (1985) J Chrom 347: 1–10
O'Shannessy DJ, Andersson LI and Mosbach K (1989) J Mol Recog 2: 1–5
Kempe M and Mosbach K (1991) Analyt Lett 24: 1137–45
Sellergren B and Shea KJ (1993) J Chrom submitted
Shea KJ, Spivak DA and Sellergren B (1993) J Amer Chem Soc 115: 3368–9
Dunkin IR, Lenfeld J and Sherrington DC (1993) Polymer 34: 77–84
Sagiv J (1979) Isr J Chem 18: 346–53
Wulff G, Heide B and Helfmeier G (1986) J Amer Chem Soc 108: 1089–91
Toa Y-T and Ho Y-H (1988) J Chem Soc Chem Commun 417–8
Tahmassebi DC and Sasaki T (1992) Abstr Amer Chem Soc 204: Aug, 314 (ORGN)
Wulff G and Görlich T, private communication
Norrloew O, Månsson M-O and Mosbach K (1987) J Chrom 396: 374–77
Wulff G, Lauer M and Disse B (1979) Disse Chem Ber 112: 2854–65
Wulff G, Heide B and Helfmeier G (1987) React Polym Ion Exch Sorb 6: 299–310
Shea KJ and Sasaki DY (1991) J Amer Chem Soc 113: 4109–21
Kljatschenko WA (1951) Dokl Acad Nauk S.S.S.R. 81: 235ff
Stanberg J, Seidl J and Rahn J (1958) J Polym Sci (1958) B 31: 15–24
Nishide H, Deguchi J and Tsuchida E (1976) Chem Lett 2: 169–74
Nishide H, Deguchi J and Tsuchida E (1977) J Polym Sci Polym Chem 15: 3023–9
Nishide H and Tsuchida E (1976) Makromol Chem 177: 2295–310
Kato M, Nishide N, Tsuchida E and Sasaki T (1981) J Polym Sci Polym Chem 19: 1803–9
Efendiev AA and Kabanov VA (1982) Pure Appl Chem 54: 2077–92
Kabanov VA, Efendiev AA and Orujev DD (1979) J Appl Polym Sci 24: 259–67
Gupta SN and Neckers DC (1982) J Polym Sci Polym Chem 20: 1609–22
Neckers DC (1985) Polymeric bipyridines as chelating agents and catalysts, in Metalcontaining polymer systems, Seats JE, Carraher CE, Pittman CU, Jr (eds), Plenum Press NY, London
Kuchen W and Schram J (1988) Angew Chem Int Ed Engl 27: 1695–7
Harkins DA and Schweitzer GK (1991) Sep Sci Techn 26: 345–55
Tsukagashi K, Yu KY, Maeda M and Takagi M (1993) Bull Chem Soc Jpn 66: 114–20
Chanda M and Rempel GL (1992) React Polym 16: 149–58
Choi KS (1990) Makromol Chem Makromol Symp 33: 55–63
Rosatzin T, Andersson LI, Simon W and Mosbach K (1991) J Chem Soc Perkin Trans II 8: 1261–7
Bidan G, Divisia-Blohorn B, Lapkowski M, Kern J-M and Sauvage J-P (1992) J Amer Chem Soc 114: 5986–94
Belokon YN, Tararov I, Savel'eva TF, Vorob'ev MM, Vitt SV, Sizoy VF, Sukhacheva NA, Vasil'ev GV and Belekov VM (1983) Makromol Chem 184: 2213–23
Fuji Y, Matsutani K and Kilkuchi K (1985) J Chem Soc Chem Commun 415–7
Fuji Y, Matsutani K, Ota M, Adachi M, Savoji I, Haneishi and Kuwana Y (1984) Chem Lett 1487–90
Dhal PK and Arnold FH (1991) J Amer Chem Soc 113: 7417–8
Yamamura K, Hatakeyama H, Naha K, Tabushi I (the late) and Kurihara K (1988) J Chem Soc Chem Commun 79–81
Byström SE, Börje A and Akermark B (1993) J Amer Chem Soc 115: 2081–3
Sarhan A, Abou M and El-Zabah (1987) Makromol Chem Rapid Commun 8: 555
Andersson LI and Mosbach K (1989) Makromol Chem Rapid Commun 10: 491–5
Hopkins A and Williams A (1983) J Chem Soc Perkin Trans II 891–6
Leonhardt A and Mosbach K (1987) React Polym Ion Exch Sorbents 6: 285–6
Robinson DK and Mosbach K (1989) J Chem Soc Chem Commun 969–70
Morihara K, Kurihara S and Suzuki J (1988) Bull Chem Soc Jpn 61: 3991–8
Morihara K, Nishihata E, Kojima M and Miyake S (1988) Bull Chem Soc Jpn 61: 3999–4003
Shimada T, Nakamishi K and Morihara K (1992) Bull Chem Soc Jpn 65: 954–8
Morihara K, Tanaka E, Takeuchi Y, Miyazaki K, Yamamoto N, Sagawa Y, Kawamoto E and Shimida T (1989) Bull Chem Soc Jpn 62: 499–505
Morihara K, Kurokawa M, Kamata Y and Shimada T (1992) J Chem Soc Chem Commun 358–60
Morihara K, Kawasaki S and Kofuji M and Shimada T (1993) Bull Chem Soc Jpn 66: 906–13
Muller R, Andersson LI and Mosbach K (1993) Makromol Chem Rapid Comm 14: 637
Shokat KM, Leumann CJ, Sugasaware R and Schultz PG (1989) Nature 338: 169
Klibanov AM (1989) Trends Biochem Sci 14: 141
Russell AJ and Klibanov AM (1988) J Biol Chem 263: 1624–6
Braco L, Dabulis K and Klibanov AM (1990) Proc Natl Acad Sci 87: 274–7
Dabulis K and Klibanov AM (1992) Biotech Bioeng 39: 176–85
Ståhl M, Månsson M-O and Mosbach K (1990) Biotech Lett 12: 161–6
Ståhl M, Jeppssonwistrand U, Månsson M-O and Mosbach K (1991) J Amer Chem Soc 113: 9366–8
Ståhl M, Månsson M-O and Mosbach K (1993) Protein Eng 6: 51–51
Kriegel T, Schellenberger W, Kopfschläger G and Hoffmann E (1991) Biomed Biochim Acta 50: 1159–65
Schultz PG (1989) Angew Chem Int Ed Engl 28: 1283–95
Green BS (1991) Curr Opin Biotech 2: 395–400
Rini JM, Schulzegahmen U and Wilson IA (1992) Science 255: 959–66
Tramontano A, Janda KD and Lerner RA (1986) Proc Natl Acad Sci 83: 6736–40
Pollack SJ, Jacobs JW and Schultz PG (1986) Science 234: 1570–3
Winteer G and Milstein C (1991) Nature 349: 293–9
Lerner RA, Kang AS, Bain JD, Burton DR and Barbas CF (1992) Science 285: 1313
Tawfik DS, Zemel RR, Arrad-Yellin R, Green BS and Eshhar Z (1990) Biochemistry 29: 9916–21
Shokat KM, Ko MK, Scanlin TS, Kochersperger L, Yonkovich L, Thaisrivongs S and Schultz PG (1990) Angew Chem Int. Ed Engl 29: 1296–1303.
Reymond JL, Janda KD and Lerner RA (1991) Angew Chem Int Ed Engl 30: 1711–3
Iverson BI, Cameron KE, Jahangiri GK and Pasternak DS (1990) J Amer Chem Soc 112: 5320–3
Iverson BL and Lerner RA (1989) Science 243: 1184–8
Scanlan TS, Prudent JR and Schultz PG (1991) J Amer Chem Soc 113: 9397–8
Sinha SC, Keiman E and Reymond J-L (1993) J Amer Chem Soc 115: 4893–4
Liotta LJ, Benkovic PA and Miller GP (1993) J Amer Chem Soc 115: 350–1
Braisted AC and Schultz PlG (1990) J Amer Chem Soc 112: 7430–1
Keinan E, Sinha SC, Sinha-Bagchi A, Benory E, Ghozi MC, Eshhar Z and Green BS (1990) Pure Appl Chem 62: 2013–9
IKeda S, Weinhouse MI, Janda KD, Lerner RA and Danishefsky SJ (1991) J Amer Chem Soc 113: 7763–4
Jackson DY, Liang MN, Bartlett PA and Schultz PG (1992) Angew Chem Int Ed Engl (1992) 3: 182–3
Jackson JR, Prudent JR, Kochersperger L, Yonkovich S and Schultz PG (1992) Science 256: 365–7
Uno T and Schultz PG (1992) J Amer Chem Soc 114: 6573–4
Fernholz E, Schloeder D, Liu KKC, Bradshaw CW, Huang HM, Janda KD, Lerner RA and Wong CH (1992) J Org Chem 57: 4756–61
Gibbs RA, Taylor S and Benkovic SJ (1992) Science 258: 803–6
Jackson DY, Prudent JR, Baldwin EP and Schultz PG (1991) Proc Natl. Acad Sci 58: 58–62
Shea KJ, Stoddard GJ, Shavelle DM, Walmi F and Choate MM (1990) Macromols 23: 4497–507
Shea KJ, Thompson EA, Pandy SD and Beauchamp PS (1980) J Amer Chem Soc 102: 3149–3155
Csaba G, Kovács P, László V (1989) Acta Protozoologica 28: 175–82
Wulff G, Private Communication
Wulff G and Stellbrink H (1990) Rec Trav Chim Payes-Bas (J Roy Soc Neth Chem Soc) 109: 216–21
Gelfi C and Righetti PG (1981) Electrophoresis 2: 220–28
Wu TF and Orgel LE (1992) J Amer Chem Soc 114: 5496–500
Wu TF and Orgel LE (1992) J Amer Chem Soc 114: 7963–8
Rosenberg J-E and Flodin P (1987) Macromols 20: 1518–22
Rosenberg J-E and Flodin P (1986) Macromols 19: 1543–6
Hoss R and Vogtle F (1994) Angew Chem Int Edn Engl 33: 375
Mullis KB, Scientific American, April 1990, p 56
Erlich HA, Gelfand D and Sninsky JJ, Science (1991) 252: 1643
Brock TD and Freeze H J. Bacteriol (1969) 98: 289
Saiki RK, Science (1988) 239: 487
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Steinke, J., Sherrington, D.C., Dunkin, I.R. (1995). Imprinting of synthetic polymers using molecular templates. In: Synthesis and Photosynthesis. Advances in Polymer Science, vol 123. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-58908-2_3
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