ISSN:
0170-2041
Keywords:
N-Iodosuccinimide
;
α-O-Glycopeptide
;
2-Deoxy-α-O-glycosided, deiodination, deprotection of
;
Peptides
;
Carbohydrates
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Synthesis of 2-Deoxy-α-O-glycopeptides by the N-Iodosuccinimide (NIS) ProcedureGlycosidation of amino acid/peptide derivatives of serine, threonine, or hydroxyproline with glycals like tris-O-acetyl-D-glucal 1 or tris-O-acetyl-D-galactal 2 and N-iodosuccinimide (NIS) gives 2-deoxy-2-iodo-α-O-glycopeptides with high yields and excellent anomeric purity. Disaccharide glycals like per-O-acetyl-D-cellobial 15, per-O-acetyl-D-lactal 16, and 2′,3′,4′,6′-tetra-O-acetyl-β-D-galactopyranosyl-(1 - 3)-4,6-di-O-benzyl-D-galactal 17 can also be used as glycosyl donors in this process. They give moderate to good yields of α-O-glycoside with formation of small amounts of β-O-glycopeptide. The NIS procedure is especially favored for the direct and stereoselective glycosidation of larger peptide fragments, which is very difficult with classical techniques. The so-formed 2-deoxy-2-iodo-α-O-glycopeptides were deiodinated by using different methods and then deacetylated in the sugar moiety.
Additional Material:
5 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.1991199101127
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