Development of convergent methodology to access a broad range of glycopeptides as a firm basis of chemical biology.
Project/Area Number |
24750154
|
Research Category |
Grant-in-Aid for Young Scientists (B)
|
Allocation Type | Multi-year Fund |
Research Field |
Chemistry related to living body
|
Research Institution | Toho University (2013) Tohoku University (2012) |
Principal Investigator |
|
Project Period (FY) |
2012-04-01 – 2014-03-31
|
Project Status |
Completed (Fiscal Year 2013)
|
Budget Amount *help |
¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Fiscal Year 2013: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2012: ¥2,730,000 (Direct Cost: ¥2,100,000、Indirect Cost: ¥630,000)
|
Keywords | ペプチド / 糖 / 核酸 / 糖タンパク質 / チオカルボン酸 / チオエステル / 糖ペプチド / 糖タンパク |
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.
|
Report
(3 results)
Research Products
(8 results)
-
[Journal Article] Total synthesis of vineomycin B22013
Author(s)
S. Kusumi, S. Tomono, S. Okuzawa, E. Kaneko, T. Ueda, K. Sasaki, D. Takahashi, K. Toshima
-
Journal Title
Journal of the American Chemical Society
Volume: 135
Issue: 42
Pages: 15909-15912
DOI
Related Report
Peer Reviewed
-
[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.
-
Journal Title
Bioorg. Med. Chem., Elsevier
Volume: 21
Issue: 12
Pages: 3479-3485
DOI
Related Report
Peer Reviewed
-
-
-
-
-
-