N-linked solid phase peptide synthesis

Tetrahedron Letters

Volumn 39, Issue 24, 1998, Pages 4171-4174

  Léger, Roger ^a   Yen, Rose ^a   She, Miles W ^a   Lee, Ving J ^a   Hecker, Scott J ^a  

^a Microcide Pharmaceuticals Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,4 DINITROPHENOL; PEPTIDE; RESIN;

ARTICLE; CARBOXY TERMINAL SEQUENCE; CHEMICAL BOND; PEPTIDE SYNTHESIS; REACTION ANALYSIS;

EID: 0032508073     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00777-1     Document Type: Article

References (24)

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15. nd Ed., Pierce Chemical Company, Rockford, Illinois 1984, pp 12-13.
16. 5. Both phenyl carbonate and imidazole carbamate were prepared and test reactions were done by (1) treating a known amount of 2 with benzylamine and (2) cleaving off the benzylamine and weighing it as its TFA salt. Thus p-nitrophenyl carbonate was found to give the best loading of 0.7 mmol/g.
17. -1 for carbamates.
18. 7. The lithium salts are prepared by dissolving the amino acid and LiOH (1 eq.) in water and lyophilizing the solution.
19. 8. At this point, the phenylalanine was cleaved to measure the loading and it was found to be 0.7 mmol/g.
20. 9. Takahashi, S.; Kobuko, M.; Satake, K., Chem. Lett. 1983, 1445-1448.
21. 10. PRLPS column with 20 to 60 % gradient of acetonitrile in 0.1% aqueous TFA over 20 min.
22. 2O) δ 8.47 (s, 1H), 7.34 (m, 3H), 7.18 (m, 3H), 4.40 (m, 4H), 3.135 (m, 4H).
23. 12. Lysine and ornithine peptides were prepared from ε- and δ-Boc protected amino acids respectively, with a free α amino function.
24. 13. Epimerization may take place through an azlactone intermediate. Benoiton, N. L., Chen, F. M. F., Can. J. Chem. 1981, 59, 384-389.