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Synthesis and Characterization of (5′‐Deoxyadenosin‐5′‐yl)cobalamin ( = ‘Adenosylcobalamin’) Analogues Mimicking the Transition‐State Geometry of Coenzyme‐B 12 ‐Dependent Rearrangements
Author(s) -
Poppe László,
Rétey János,
Hull William E.
Publication year - 1993
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19930760623
Subject(s) - chemistry , adenosylcobalamin , moiety , cobalamin , stereochemistry , cofactor , methylcobalamin , crystallography , enzyme , organic chemistry , biochemistry , vitamin b12
A convergent synthesis of the five novel analogues 1a–e of (5′‐deoxyadenosin‐5′‐yl)cobalamin ( = ‘adenosylcobalamin’) is described. The analogues 1a–e carry oligomethylene chains (C 3 –C 7 ) inserted between the central Co‐atom and the 5′‐O‐atom of the adenosine moiety and are thought to mimick the transition‐state geometry in coenzyme‐ B 12 ‐catalyzed rearrangement. All five analogues were characterized by NMR, UV, and FAB mass spectrometry.