Pub No:
3
Title:
The Reaction of Cobalamins with Thiols: an Alternative Synthesis of Alkyl-cobamide Coenzyme Analogues
Authors:
David Dolphin and AW Johnson
Journal:
Proc. Chem. Soc.
Year:
1963
Pages:
311-312
Abstract:
Aqeous solutions of hydroxocobalamin change from red to violet in color when treated with one of the following: 2-mercaptoethanol, mercaptoacetic acid, cysteine, homocysteine, ethanethiol, PhCH2SH, and NaHS. Subsequent addition of MeI in the dark afforded methylcobalamin, which was identified by chromatography and spectra. With NaHS the yield is 90%. Other successful alkylating agents were p-MeC66H4SO3Me, 1-chloro-, 1-bromo-, and 1-iodopropane, 1-iodobutane, chloroacetic acid, α-chloropropionic acid, and acetyl chloride.

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