Abstract
Di-t-butyl dicarbonate and one of its dithiol analogs, practical methods of preparation for which are given, react with amino-acid esters to form the N-t-butoxycarbonyl (t-BOC) derivatives and the thiol analogs in good yield under mild conditions. The thiol analogs are stable to acidic conditions, which rapidly remove the t-BOC group itself. t-Butyl trimethylsilyl carbonate forms a (CH3)3Si ether from a N-thiol-t-BOC serine methyl ester. The N-thiol-t-BOC group can be removed from the —NHCOSR (R = t-butyl) by heating with peroxide-acetic acid.
Action of the dicarbonates described above has not been attended by racemization in the cases examined. The two dicarbonates may be useful as agents for selective blocking and deblocking of amino or other groups.
Keywords: blocking groups, peptide synthesis
Full text
PDF
Selected References
These references are in PubMed. This may not be the complete list of references from this article.
- Leonard N. J., McDonald J. J., Henderson R. E., Reichmann M. E. Reaction of diethyl pyrocarbonate with nucleic acid components. Adenosine. Biochemistry. 1971 Aug 31;10(18):3335–3342. doi: 10.1021/bi00794a003. [DOI] [PubMed] [Google Scholar]
- Leonard N. J., McDonald J. J., Reichmann M. E. Reaction of diethyl pyrocarbonate with nucleic acid components. I. Adenine. Proc Natl Acad Sci U S A. 1970 Sep;67(1):93–98. doi: 10.1073/pnas.67.1.93. [DOI] [PMC free article] [PubMed] [Google Scholar]
- Melchior W. B., Jr, Fahrney D. Ethoxyformylation of proteins. Reaction of ethoxyformic anhydride with alpha-chymotrypsin, pepsin, and pancreatic ribonuclease at pH 4. Biochemistry. 1970 Jan 20;9(2):251–258. doi: 10.1021/bi00804a010. [DOI] [PubMed] [Google Scholar]