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Synthesis of a 15N, 13C-labeled lactam analog of a GM4-lactone cell-surface glycolipid

✍ Scribed by Brian A. Salvatore; James H. Prestegard

Book ID
104260302
Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
225 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis

A ~ZC and ~5N-iabeled lactam analog of a naturally occurring GM4 lactone glycolipid was synthesized in a convergent manner. The 13C-labels in the sialic acid portion of the molecule were derived from uniformly 13C-labeled pyruvate, and the ISN was introduced using a sulfonylamidoglycosylation reaction with labeled benzenesulfonamide.

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Synthesis and characterization of a 13C-
Synthesis and characterization of a 13C-labeled Ξ±-mannosyl glycolipid analog from [13C]glucose
✍ Brian J. Hare; Charles R. Sanders II; Stephen E. McIntyre; James H. Prestegard πŸ“‚ Article πŸ“… 1993 πŸ› Elsevier Science 🌐 English βš– 248 KB

A method is described for the synthesis of a [13C]c~-mannosyl glycolipid analog from [13C]glucose. After acetylation and reduction of glucose (U-13C6, 30%) to tri-O-acetyl-D-glucal (U-13C6, 30%), addition of the nucleophile 2-[2-[2-[2-(tetradecyloxy)ethoxy]ethoxy]ethoxy]-ethanol (tetra-decyltetragly