Solid-Phase Synthesis with Glycosyltransferases

Claudine Auge, Christine Le Narvor, and Andre Lubineau 

Solid-phase synthesis has several advantages over traditional solution-based methods. Firstly, large excesses of reagents can be used so that the coupling steps can be repeated to drive reactions to completion. Secondly, products are isolated at each step by simple filtration, an obvious simplification of the work-up procedures, which might enable future automation. 

---

The improved availability of glycosyltransferases has led to increased use of che-moenzymatic synthesis, where chemical synthesis is combined with the use of glycosyltransferases to build up saccharides on a parent glycopeptide in solution or on solid phase (Section 6.3.3.6).1200"2061... 

Various synthetic routes to novel nucleoside diphosphate derivatives have been described. Tonn and Meier describe a solid-phase protocol for the synthesis of cjc/oSal-protected nucleoside monophosphates, which can then be used for the synthesis of diphosphates and triphosphates, and conjugates of both, by treatment with the appropriate phosphate or pyrophosphate derivative, including methylene pyrophosphate derivatives. " A synthesis of lamivudine (3TC) diphosphate has been reported which involves oxidation of lamivudine /f-phosphonate, conversion of the phosphate to its imidazolate followed by reaction with phosphate. A few syntheses of glycosyl conjugates of nucleoside diphosphates, e.g. (17), have been reported for their study with glycosyltransferases, which play a key role in a variety of cellular processes. ... 

---