2013 Fiscal Year Final Research Report
Development of convergent methodology to access a broad range of glycopeptides as a firm basis of chemical biology.
| Project/Area Number |
24750154
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| Research Category |
Grant-in-Aid for Young Scientists (B)
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| Allocation Type | Multi-year Fund |
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| Research Field |
Chemistry related to living body
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| Research Institution | Toho University (2013)
Tohoku University (2012) |
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Principal Investigator |
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| Project Period (FY) |
2012-04-01 – 2014-03-31
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| Keywords | ペプチド / 糖 / 核酸 / 糖タンパク質 |
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| Research Abstract |
Novel convergent synthetic methodologies to prepare proteins with post-translational modifications were developed. We found out that methylphenacyl thioesters are stable enough to be carried through standard Boc-TFA peptide elongation as a precursor of thioacids, and can be deprotected into the corresponding thioacids easily and cleanly. The thioacids prepared can be converted into amide bonds when treated with N-carbonyl cyclic amino acid anhydrates. We also developed a novel chemical ligation at the site of asparagine using oligopeptides with N-terminal N-Boc-protected beta-thioaspartic acid and C-terminal acyl azide respectively. The reaction proceeds via addition accompanied by loss of nitrogen and sulfur to give the corresponding asymmetrical imide, and deprotection of the Boc group, followed by a spontaneous N to N acyl shift.
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[Journal Article] Exploration of an imide capture/N,N-acyl shift sequence for asparagine native peptide bond formation2013
Author(s)
Mhidia, R.; Boll, E.; Fécourt, F.; Ermolenko, M.; Ollivier, N.; Sasaki, K.; Crich, D.; Delpech, B.; Melnyk, O.
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Journal Title
Bioorg. Med. Chem., Elsevier
Volume: 21
Pages: 3479-3485
DOI
Peer Reviewed
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