C-Glycosyl Tyrosines. Synthesis and Incorporation into C-Glycopeptides

Autor:	Sharn Ramaya, Graham B. Bloomberg, Alan J. Pearce, Timothy Gallagher, Simon N. Thorn, Daryl S. Walter
Rok vydání:	1999
Předmět:	chemistry.chemical_classification Glycal Stereochemistry Aryl Organic Chemistry Iodide carbohydrates (lipids) chemistry.chemical_compound chemistry Reagent Peptide synthesis Moiety Glycosyl Lewis acids and bases
Zdroj:	The Journal of Organic Chemistry. 64:5453-5462
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo990253e
Popis:	The synthesis of the Fmoc-protected C-glycosyl tyrosines 1 and 2, together with two other related C-glycosyl tyrosines, has been achieved. Key reactions involved (i) the reaction of a glycal with an organozinc reagent (carrying an aryl iodide function) in the presence of a Lewis acid to establish the C-glycosyl linkage and (ii) subsequent cross coupling of the aryl iodide to an alanyl zinc reagent (in the presence of a Pd(0) catalyst) to complete the construction of the alpha-amino acid moiety. Using solid-phase peptide synthesis methods, two units of the mannosyl derivative 1 (shown as L-Tyr[C-Ac(4)-alpha-D-Man]) have been incorporated (with four units of glycine) into the linear hexapeptide 3 which was then converted to the C(2)-symmetric cyclic oligopeptide 4.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::54b017c7e67357da1f6371ce41e69b2c https://doi.org/10.1021/jo990253e Zobrazit plný text záznamu