Acyl disulfide-mediated intramolecular acylation for orthogonal coupling between unprotected peptide segments. Mechanism and application

Tetrahedron Letters

Volumn 37, Issue 7, 1996, Pages 933-936

  Liu, Chuan Fa ^a   Rao, Chang ^a   Tam, James P ^a  

^a VANDERBILT UNIVERSITY MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PEPTIDE SYNTHESIS; REACTION ANALYSIS;

EID: 0030033749     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02394-1     Document Type: Article

References (15)

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2. (b) Kemp, D. S. and Carey, R. I. Tetrahedron Lett. 1991, 32, 2845-2848.
3. (c) Kemp, D. S.; Carey, R. I. J. Org. Chem. 1993, 58, 2216-2222.
4. (a) Liu, C. F. and Tam, J. P. J. Am. Chem. Soc. 1994, 116, 4149-4153.
5. (b) Liu, C. F. and Tam, J. P. Proc. Natl. Acad. Sci. USA 1994, 91, 6584-6588.
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9. (a) Matsueda, R. and Aiba, K. Chem. Lett. 1978, 951-952.
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11. Ellman, G. L. Arch. Biochem. Biophys. 1959, 82, 70-77.
12. Ac-Ala-Phe-SH was reacted with Tfa. H-Cys(Npys)Ala-OMe and the product was analyzed by reverse phase HPLC which revealed no Ac-Ala-D-Phe-Cys-Ala-OMe for which the retention time was known from an authentic product.
13. Tam, J. P., Lu, Y.-A, Liu, C.-F. and Shao, J. Proc. Natl. Acad. Sci. USA. In press.
14. (a) Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149-2154.
15. (b) Barany, G., and Merrifield, R. B.: Solidphase peptide synthesis. In The Peptides, Vol 2; Gross, E.; Meienhofer, J. Eds.; Academic Press: New York, 1979, pp. 1-284.