A-linked glycopeptides

The advantages of the methoxyethyl ester over some of the other water-solubilizing esters are that many of the amino acid esters are crystalline and thus easily purified, are cleaved with a number of readily available lipases, and are useful for the synthesis of A-linked glycopeptides. ... 

Scheme 2.22 Synthesis of A-linked glycopeptides on a solid support.

M Meldal, B Klaus. Pentafluorophenyl esters for temporary carboxyl group protection in solid phase synthesis of A-linked glycopeptides. Tetrahedron Lett 48, 6987, 1990. 

J. M. Hogan, S. J. Pitteri, P. A. Chrisman, and S. A. McLuckey, Complementary structural information from a tryptic A-linked glycopeptides via electron transfer ion/ion reactions and collision-induced dissociation, J. Proteome Res., 4 (2005) 628-632. 

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

Great effort has been focused on the synthesis of A -linked glycopeptides because of the important role of A -linked saccharides in glycoproteins, with impressive results being reported during the last 10 to 20 years (reviewed in Refs. [37,38,144,145]). As mentioned in Section 15.2.1, two basic strategies exist for preparation of A-linked glycopeptides ... 

SCHEME 15.24 Convergent synthesis of A -linked glycopeptides by coupling of solid-supported peptide 191 to chitobiosyl amine 192 followed by cleavage and deprotection. 

Vetter, D, Tumelty, D, Singh, S K, Gallop, M A, A versatile solid-phase synthesis of A-linked glycopeptides, Angew. Chem. Int. Ed., 34, 60-62, 1995. 

Offer, J, Quibell, M, Johnson, T, On-resin solid-phase synthesis of asparagine A-linked glycopeptides use of V-(2-acetoxy-4-methoxybenzyl) (AcHmb) aspartyl amide-bond protection to prevent unwanted aspartimide formation, J. Chem. Soc. Perkin Trans. 1, 175-182, 1996. 

Holm, B, Linse, S, Kihlherg, J, Synthesis of an A-linked glycopeptide from vitamin K-dependent protein S, Tetrahedron, 54, 11995-12006, 1998. 

Christiansen-Brams, I, Meldal, M, Bock, K, Protected-mode synthesis of A-linked glycopeptides Single-step preparation of building blocks as peracetyl glycosylated Na Fmoc asparagine OPfp esters, J. Chem. Soc. Perkin Trans. 1, 1461-1471, 1993. 

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