Stereoselective synthesis of a pyridoxamine coenzyme-amino acid chimera: Assembly of a polypeptide incorporating the pyridoxamine moiety

Tetrahedron Letters

Volumn 37, Issue 13, 1996, Pages 2129-2132

  Sinha Roy, Ranabir ^a   Imperiali, Barbara ^a  

^a California Institute of Technology ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; CHIMERIC PROTEIN; PYRIDOXAMINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; PEPTIDE SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0343897944     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00207-9     Document Type: Article

References (11)

1. Imperiali, B.; Sinha Roy, R. J. Am. Chem. Soc. 1994, 116, 12083-12084.
2. Imperiali, B.; Sinha Roy, R. J. Org. Chem. 1995, 60, 1891-1894.
3. Imperiali, B.; Sinha Roy, R.; Walkup, G. K.; Wang, L. Unnatural Amino Acids for the Design of Functional Proteins: Biomimetic Catalysis Using Coenzyme Amino Acids. In NATO Series on Biomimetic Catalysis; Wilcox, C. S. Ed.; Kluwer Academic Pub.; Dordrecht, 1995; in press.
4. Imperiali, B.; Sinha Roy, R.; Wang, L. Peptidyl Models for Coenzyme Catalysis. In Peptides Chemistry, Structure, and Biology (Proc. 14th Amer. Pep. Symp.); Escom Science Pub.; Leinden, 1995; in press.
5. Nefkens, G. H. L.; Zwanenburg, B. Tetrahedron 1983, 39, 2995-2998.
6. Trost, B. M.; Caldwell, C. G. Tetrahedron Lett. 1981, 22, 4999-5002.
7. Myers, A. G.; Gleason, J. L.; Yoon, T. Y. J. Am. Chem. Soc. 1995, 117, 8488-8489.
8. Myers, A. G.; Yoon, T.; Gleason, J. L. Tetrahedron Lett. 1995, 36, 4555-4558.
9. 3 647.2843, obsd 647.2828.
10. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; John Wiley and Sons, Inc.; New York, 1991; pp 88-92.
11. Identity of the peptide was confirmed by NMR and HRMS analyses. In addition, the UV signature of the Pam residue closely matches that of the pyridoxamine cofactor.