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.
journal_name
Bioorg Med Chem Lettjournal_title
Bioorganic & medicinal chemistry lettersauthors
Sun C,Luo G,Neravetla S,Ghosh SS,Forood Bdoi
10.1016/j.bmcl.2013.06.095subject
Has Abstractpub_date
2013-09-15 00:00:00pages
5203-8issue
18eissn
0960-894Xissn
1464-3405pii
S0960-894X(13)00828-7journal_volume
23pub_type
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