Enzymatic Synthesis of Glycopeptides

2 Enzymatic Synthesis of Glycopeptides Use of ControUed-Pore Glass 

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Thayer DA, Wong C-H (2007) Enzymatic Synthesis of Glycopeptides and Glycoproteins. 267 37-63... 

The enzymatic synthesis of glycopeptides does not require protection of the functional groups of the amino acid side chains and sugar hydroxyls, because of the high stereoselectivity and regioselectivity of proteases. However, the substrate selectivity of these enzymes may limit a wider range of applications. 

Schuster M, Wang P, Paulson JC, Wong CH, Solid-phase chemical-enzymatic synthesis of glycopeptides and oligosaccharides, J. Am. Chem. Soc., 116 1135-6, 1994. 

Meldal, M, Auzanneau, F-I, Hindsgaul, O, Palcic, M M, A PEGA resin for use in the solid-phase chemical-enzymatic synthesis of glycopeptides, J. Chem. Soc. Chem. Commun., 1849-1850, 1994. 

Scheme 14.1 Strategies for glycopeptide library synthesis Strategy 1 chemical or enzymatic glycosylation of peptide or glycopeptide Strategy 2 the building-block approach. While enzymes have not yet been used in the solid-phase synthesis of glycopeptide libraries, several resin-bound glycopeptides have been glycosylated enzymatically.36,114...

The major method for enzymatic synthesis of A-linked glycopeptides/glycoproteins is to elaborate the existing sugar moieties on the proteins. 

Wang LX, Tang M, Suzuki T, Kitajima K, Inoue Y, Inoue S, Fan JQ, Lee YC. Combined chemical and enzymatic synthesis of a C-glycopeptide and its inhibitory activity toward glycoamidases. J. Am. Chem. Soc. 1997 119 11137-11146. 

Remarkable advances have been made in the synthesis of N- and O-glycosylated amino acids that, in addition to the 5-fattyacyl-cysteine, are the most sensitive derivatives to the conditions of peptide synthesis. The fine tuning of both carbohydrate and peptide chemistry as well as the use of enzymatic methods are required for the synthesis of glycopeptides. " Similarly soft chemistry has to be applied in the case of S-acylated peptides, whereas fat-tyacylation at amino groups raises no additional difficulties.The state of the art in the field of glyco- and lipopeptide synthesis is discussed in details in Vol. E22b, Sections 6.3 and 6.4, respectively. 

Chemical synthesis of glycopeptides which carry large oligosaccharide residues is often demanding and time-consuming. In such cases, use of enzymatic techniques for the elaboration of existing,... 

Sallas, F, Nishimura, S-I, Chemo-enzymatic synthesis of glycopolymers and sequential glycopeptides hearing lactosamine and sialyl Lewis unit pendant chains, J. Chem. Soc. Perkin Trans. 1, 2091-2103, 2000. 

Ichikawa Y (1997) Enzymatic synthesis of ohgosaccharides and glycopeptides. In Large DG, Warren CD (eds) Glycopeptides and related compounds. Marcel Dekker, New York, p 79... 

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