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Synthesis of {[A15‐ 13 C]5′‐deoxy‐ N 1‐methyladenosylcobalamin + }Cl −
Author(s) -
Brown Kenneth L.,
Xia Zuping
Publication year - 2000
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/1099-1344(200006)43:7<635::aid-jlcr348>3.0.co;2-c
Subject(s) - chemistry , stereochemistry , methylation , anomer , cobalamin , ribose , organic chemistry , vitamin b12 , biochemistry , enzyme , gene
The synthesis of {[A15‐ 13 C]5′‐deoxy‐ N 1‐methyladenosylcobalamin + }Cl − , an analog of coenzyme B 12 , was accomplished by glycosidation of [5‐ 13 C] d ‐ribose with 4‐pentenol, followed by benzoylation, coupling to N 6 ‐benzoylaminopurine, deprotection, chlorination at C5′, methylation at N 1, and oxidative addition to reduced cobalamin. The α and β anomers of the intermediate pent‐4‐enyl‐ erythro ‐furanosides were detected and quantified for the first time. Copyright © 2000 John Wiley & Sons, Ltd.