Enzymes — in particular aldolases — are not only a supplement to classical methodologies, but also useful tools in many fields of aldol additions where classical synthetic procedures fail. This is the area of the synthesis of amino acids1,2 and carbo-hydrates.3,4,5,6,7,8 in the traditional sense. But more and more aldolases are used in C—C bond formation processes. Examples in natural product synthesis are given in Schetter and Mahrwald.9 Moreover, the combination of these two different synthetic strategies — the enzymatic route and the classical organic synthetic route — represent a valuable tool for the construction of defined stereogenic centres of natural products.10
Natural occurring aldolases are classified by their mode of action into two main groups: class I and class II aldolases. The accepted reaction mechanism of these two groups is shown below. Class I aldolases bind substrates via imine-enamine formation with a lysine residue of the active site of the enzyme. This step initiates the C—C bond formation process with an aldehyde and subsequent hydrolysis sets the aldol adduct free (Scheme 3.6.1).
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References
Gröger H, Drauz K (2004) In: Asymmetric Catalysis on Industrial Scale, Blaser HU, Schmidt E (eds). Wiley-VCH, Weinheim, p 131
Liljeblad A, Kanerva LT (2006) Tetrahedron 62:5831
Gijsen HJM, Qiao L, Fitz W, Wong CH (1996) Chem Rev 96:443
Fessner WD, Helaine V (2001) Curr Opin Biotechnol 12:574
Whalem LJ, Wong CH (2006) Aldrichimica Acta 39:63
Tolbert TJ, Wong CH (2004) Encyclopedia of Biological Chemistry 1:307
Hanson S, Best M, Bryan MC, Wong CH (2004) Trends in Biochemical Sciences 29:656
Fessner WD (200) In: Stereoselective Biocatalysis, Lennarz WJ, Lane MD (eds). Elsevier, Oxford, p 239
Schetter B, Mahrwald R (2006) Angew Chem Int Ed 45:7506
Ikunaka M (2007) Org Proc Res Dev 11:495
(a) Fessner WD (2008) In: Asymmetric Organic Synthesis with Enzymes, Gotor V, Alfonso I, Garcia-Urdiales E (eds). Wiley-VCH, Weinheim, p 275
(b) List B (2007) In: Asymmetric Synthesis, Christmann, Bräse (eds). Wiley-VCH, Weinheim, p 161;
(c) Sukumaran J, Hanefeld U (2005) Chem Soc Rev 34:530
(d) Fessner WD (2004) In: Modern Aldol Reactions, Mahrwald R (ed). Wiley VCH, Weinheim, vol 1, p 201
(e) Silvestri MG, Desantis G, Mitchell M, Wong CH (2003) Top Stereochem 23:267
(f) Roberts SM (2001) J Chem Soc Perkin Trans 1:1475
Hendrix M, Wong CH (1999) Bioorg Chem: Carbohydrates 198
Hendrix M, Wong CH (1999) Bioorg Chem: Carbohydrates 569
Kim MJ, Hennen WJ, Sweers HM, Wong CH (1988) J Am Chem Soc 10:6481
Sugai T, Kuboki A, Hiramatsu S, Okazaki H, Ohta H (1995) Bull Chem Soc Jpn 68:3581
DeSantis G, Zhu Z, Greenberg WA, Wong K, Chaplin J, Hanson SR, Farwell B, Nicholson LWR, Weiner CL (2002) J Am Chem Soc 124:9024
Greenberg WA, Varvak A, Hanson SR, Wong K, Huang H, Chen P, Burk MJ (2004) Proc Natl Acad Sci USA 101:5788
Reetz MT (2006) Adv Catal 49:1
Williams GJ, Woodhall T, Farnsworth LM, Nelson A, Berry A (2006) J Am Chem Soc 128:16238
Zhou P, Salleh MH, Honek JF (1993) J Org Chem 58:264
Shelton MC, Cotterill IC, Novak STA, Poonawala RM, Sudarshan S, Toone EJ (1996) J Am Chem Soc 118:2117
Cotterill IC, Shelton MC, Machemer DEW, Henderson DP, Toone EJ (1998) J Chem Soc Perkin Trans 1:1335
Shelton MC, Cotterill IC, Novak STA, Poonawala RM, Sudarshan S, Toone EJ (1996) J Am Chem Soc 118:2117
Fessner WD (1992) In: NATO ASI Series, Series C: Mathematical and Physical Sciences, 381:43
Takayama S, McGarvey GJ, Wong CH (1997) Ann Rev Microbiol 51:285
Fessner WD, Walter C (1996) Top Curr Chem 184:97
Toone EJ, Simon ES, Bednarski MD, Whitesides GM (1989) Tetrahedron 45:5365
Fessner WD, Eyrisch O (1992) Angew Chem Int Ed Engl 31:56
Fessner WD, Walter C (1996) Top Curr Chem 184:97.
Fessner WD, Sinerius G, Schneider A, Dreyer M, Schulz GE, Badia J, Aguilar J (1991) Angew Chem Int Ed Engl 30:555
Fessner WD, Sinerius G, Schneider A, Dreyer M, Schulz GE, Badia J, Aguilar J. (1991) Angew. Chem. Int. Ed. Engl. 30:555
Fessner WD, Badia J, Eyrisch O, Schneider A, Sinerius G (1992) Tetrahedron Lett 33:5231
Ziegler T, Straub A, Effenberger F (1988) Angew Chem 100:737
Fessner WD (1998) Curr Opin Chem Biol 2:85
Duncan R, Drueckhammer DG (1996) J Org Chem 61:438
Borysenko CW, Spaltenstein A, Straub JA, Whitesides GM (1989) J Am Chem Soc 111:9275
Fessner WD, Gosse C, Jaeschke G, Eyrisch O (2000) Eur J Org Chem 125
Wong CH, Alajarin R, Moris-Varas F, Blanco O, Garcia-Junceda E (1995) J Org Chem 60:7360
Fessner WD, Sinerius G (1994) Bioorg Med Chem 2:639
Chou WC, Chen LH, Fang JM, Wong CH (1994) J Am Chem Soc 116:6191
Von der Osten CH, Sinskey AJ, Barbas CF III, Pederson RL, Wang YF, Wong CH (1989) J Am Chem Soc 111:3924
Straub A, Effenberger F, Fischer P (1990) J Org Chem 55:3926
Pederson RL, Kim MJ, Wong CH (1988) Tetrahedron Lett 29:4645
Liu KKC, Kajimoto T, Chen L, Zhong Z, Ichikawa Y, Wong CH (1991) J Org Chem 56:6280
Zhou PZ, Salleh HM, Chan PCM, Lajoie G, Honek JF, Nambiar PTC, Ward OP (1993) Carb Res 239:155
Lees WJ, Whitesides GM (1992) Bioorg Chem 20:173
Romero A, Wong CH (2000) J Org Chem 65:8264
Schultz M, Waldmann H, Kunz H, Vogt W (1990) Liebigs Ann 1019
Chenevert R, Dasser M (2000) J Org Chem 65:4529
Matsumoto K, Shimagaki M, Nakata T, Oishi T (1993) Tetrahedron Lett 34:4935
Chenevert R, Lavoie M, Dasser M (1997) Can J Chem 75:68
Liu KKC, Kajimoto T, Chen L, Zhong Z, Ichikawa Y, Wong CH (1991) J Org Chem 56:6280
Wang YF, Dumas DP, Wong CH (1993) Tetrahedron Lett 34:403
Takaoka Y, Kajimoto T, Wong CH (1993) J Org Chem 58:4809
Pederson RL, Wong CH (1989) Heterocycles 28:477
Castillo JA, Calveras J, Casas J, Mitjans M, Vinardell MP, Parella T, Inoue T, Sprenger GA, Joglar J, Clapes P (2006) Org Lett 8:6067
Kajimoto T, Liu KKC, Pederson RL, Zhong Z, Ichikawa Y, Porco JA Jr, Wong CH (1991) J Am Chem Soc 113:6187
Henderson I, Laslo K, Wong CH (1994) Tetrahedron Lett 35:359
Moris-Varas F, Qian XH, Wong CH (1996) J Am Chem Soc 118:7647
Qiao L, Murray BW, Shimazaki M, Schultz J, Wong CH (1996) J Am Chem Soc 118:7653
Liu KKC, Kajimoto T, Chen L, Zhong Z, Ichikawa Y, Wong CH (1991) J Org Chem 56:6280
Moris-Varas F, Qian XH, Wong CH (1996) J Am Chem Soc 118:7647
Liu J, Hsu CC, Wong CH (2004) Tetrahedron Lett 45:2439
El Blidi L, Ahbala M, Bolte J, Lemaire M (2006) Tetrahedron: Asymm 17:2684
Eyrisch O, Fessner WD (1995) Angew Chem Int Ed Engl 34:1639
Chen L, Dumas DP, Wong CH (1992) J Am Chem Soc 114:741
Gijsen HJM, Wong CH (1995) J Am Chem Soc 117:2947
Gijsen HJM, Wong CH (1994) J Am Chem Soc 116:8422
Liu J, Wong CH (2002) Angew Chem Int Ed 41:1404
Koppert K, Brossmer R (1992) Tetrahedron Lett 33:8031
Malleron A, David S (1996) New J Chem 20:153
Matsumoto K, Shimagaki M, Nakata T, Oishi T (1993) Tetrahedron Lett 34:4935
Shimagaki M, Muineshima H, Kubota M (1993) Chem Pharm Bull 41:282
Kimura T, Vassilev VP, Shen GJ, Wong CH (1997) J Am Chem Soc 119:11734
Shibata K, Shingu K, Vassilev VP, Nishide K, Fujita T, Node M, Kajimoto T, Wong CH (1996) Tetrahedron Lett 37:2791
Saeed A, Young DW (1992) Tetrahedron 48:2507
Steinreiber J, Fesko K, Reisinger C, Schuermann M, van Assema F, Wolberg M, Mink D, Griengl H (2007) Tetrahedron 63:918
Fujii M, Miura T, Kajimoto T, Ida Y (2000) Synlett 1046
Shibata K, Shingu K, Vassilev VP, Nishide K, Fujita T, Node M, Kajimoto T, Wong C-H (1996) Tetrahedron Lett 37:2791
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(2009). Enzyme-Catalysed Aldol Addition. In: Mahrwald, R. (eds) Aldol Reactions. Springer, Dordrecht. https://doi.org/10.1007/978-1-4020-8701-1_19
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