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Bioorg Med Chem Lett. 2013 Sep 15;23(18):5203-8. doi: 10.1016/j.bmcl.2013.06.095. Epub 2013 Jul 6.

Native chemical ligation derived method for recombinant peptide/protein C-terminal amidation.

Author information

1
Amylin Pharmaceuticals, LLC, San Diego, CA 92121, USA. chengzao.sun@amylin.com

Abstract

C-terminal amidation is often a requisite structural feature for peptide hormone bio-activity. We report a chemical amidation method that converts peptide/protein thioesters into their corresponding C-terminal amides. The peptide/protein thioester is treated with 1-(2,4-dimethoxyphenyl)-2-mercaptoethyl auxiliary (1b) in a native chemical ligation (NCL) reaction to form an intermediate, which upon removal of the auxiliary with TFA, yields the peptide/protein amide. We have demonstrated the general utility of the approach by successfully converting several synthetic peptide thioesters to peptide amides with high conversion rates. Preliminary results of converting a recombinant peptide thioester to its amide form are also reported.

KEYWORDS:

1-Phenyl-2-mercaptoethyl auxiliary; C-terminal amidation; Native chemical ligation; Peptide amide; Peptide thioester

PMID:
23880540
DOI:
10.1016/j.bmcl.2013.06.095
[Indexed for MEDLINE]
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