From Glycals to Glycopeptides: A Convergent and Stereoselective Total Synthesis of a High Mannose N-Linked Glycopeptide
Zhi-Guang Wang Dr.
Laboratory for Bioorganic Chemistry Sloan-Kettering Institute for Cancer Research 1275 York Avenue, New York, N.Y. 10021 (USA) Fax: (+1) 212-772-8691
Search for more papers by this authorXuFang Zhang
Laboratory for Bioorganic Chemistry Sloan-Kettering Institute for Cancer Research 1275 York Avenue, New York, N.Y. 10021 (USA) Fax: (+1) 212-772-8691
Search for more papers by this authorDavid Live Dr.
Deptartment of Biochemistry Molecular Biol. and Biophysics University of Minnesota Minneapolis, MN 55455 (USA)
Search for more papers by this authorSamuel J. Danishefsky Prof.
Laboratory for Bioorganic Chemistry Sloan-Kettering Institute for Cancer Research 1275 York Avenue, New York, N.Y. 10021 (USA) Fax: (+1) 212-772-8691
Search for more papers by this authorZhi-Guang Wang Dr.
Laboratory for Bioorganic Chemistry Sloan-Kettering Institute for Cancer Research 1275 York Avenue, New York, N.Y. 10021 (USA) Fax: (+1) 212-772-8691
Search for more papers by this authorXuFang Zhang
Laboratory for Bioorganic Chemistry Sloan-Kettering Institute for Cancer Research 1275 York Avenue, New York, N.Y. 10021 (USA) Fax: (+1) 212-772-8691
Search for more papers by this authorDavid Live Dr.
Deptartment of Biochemistry Molecular Biol. and Biophysics University of Minnesota Minneapolis, MN 55455 (USA)
Search for more papers by this authorSamuel J. Danishefsky Prof.
Laboratory for Bioorganic Chemistry Sloan-Kettering Institute for Cancer Research 1275 York Avenue, New York, N.Y. 10021 (USA) Fax: (+1) 212-772-8691
Search for more papers by this authorThis work was supported by the National Institutes of Health (Grant Numbers AI16943/CA28824). We thank Dr. George Sukenick of the MSKCC NMR Core Facility for NMR and mass spectral analyses (NIH Grant Number: CA08748).
Abstract
A concise and totally synthetic route involving the merger of a fully deprotected glycosylamine and a minimally protected aspartic acid containing peptide has enabled the homogeneous N-linked glycopeptide 1 to be synthesized. The other key conversions in the synthesis are the progression from glycal to free oligosaccharide hemiacetal and subsequent amination with high efficiency.
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- 25 PE Sciex API-100.
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