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Synfacts 2019; 15(02): 0202
DOI: 10.1055/s-0037-1611959
Peptide Chemistry
© Georg Thieme Verlag Stuttgart · New York

Extension of Native Chemical Ligation

Contributor(s):
Hisashi Yamamoto
,
Manthena Chaithanya
Canne LE. * Bark SJ, Kent SB. H. The Scripps Research Institute, La Jolla, USA
Extending the Applicability of Native Chemical Ligation.

J. Am. Chem. Soc. 1996;
118: 5891-5896
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Further Information

Publication History

Publication Date:
18 January 2019 (online)

 
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Key words

native chemical ligation - amide bond - thioester link - polypeptides - proteins

Significance

The authors have extended the applicability of native chemical ligation (NCL) of unprotected peptide segments by the use of X-Gly and Gly-X ligation sites. This increases the number of suitable sites for NCL by a factor of three, to include more than 50 of the 400 dipeptide sequences found in proteins.


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Comment

In this NCL method, the [peptide1]αCOSR reacts with a second peptide having an Nα-[(oxy)ethanethiol] group to afford the thioester-linked product, which rearranges to form a ligation product linked by an N-substituted amide bond. In addition, the substitution on the amide bond can be removed by treatment with Zn in acidic medium.


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