Reductive methylation of proteins with sodium cyanoborohydride. Identification, suppression and possible uses of N-cyanomethyl by-products

Gidley, M.J. and Sanders, J..K.M. (1982) Reductive methylation of proteins with sodium cyanoborohydride. Identification, suppression and possible uses of N-cyanomethyl by-products. Biochemical Journal, 203 1: 331-334.

Author Gidley, M.J.
Sanders, J..K.M.
Title Reductive methylation of proteins with sodium cyanoborohydride. Identification, suppression and possible uses of N-cyanomethyl by-products
Journal name Biochemical Journal   Check publisher's open access policy
ISSN 0264-6021
1470-8728
Publication date 1982-04
Sub-type Article (original research)
Volume 203
Issue 1
Start page 331
End page 334
Total pages 4
Place of publication London, United Kingdom
Publisher Portland Press
Language eng
Abstract Reductive methylation of protein amino groups with formaldehyde and sodium cyanoborohydride is shown to give up to 25% yield of N-cyanomethyl (-CH2CN) product; on work up of the reaction this is hydrolysed back to starting amine, lowering the methylation yield. Addition of metal ions such as Ni2+, which complex with free cyanide ion, improve reductive methylation yields by suppressing by-product formation. The N-cyanomethyl group itself, produced in good yield when cyanide ion replaces cyanoborohydride, may have some value as a reversible modifier of amino groups in proteins.
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Non-UQ

Document type: Journal Article
Sub-type: Article (original research)
Collection: Centre for Nutrition and Food Sciences Publications
 
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Created: Wed, 16 Mar 2011, 20:34:00 EST