Easy preparation of bioactive peptides from the novel Nα-trifluoroethyl amino acids

Chemistry Letters

Volumn , Issue 9, 2000, Pages 1052-1053

  DesMarteau, Darryl D ^a   Montanari, Vittorio ^a  

^a CLEMSON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0034340001     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2000.1052     Document Type: Article

References (16)

1. D. D. DesMarteau and V. Montanari, Chem. Commun., 1998, 2241.
2. 2, 4 mL/g, -20 ° C) gave 27.3 g (79% overall) of 1 as transparent prisms, mp 77-79 °C, dec. 105-120 °C (TGA, 5 °C/min).
3. 2 in place of triflic acid, but 1 requires more strictly anhydrous conditions until workup. Compound 1 extends the reactions of 6 to aqueous systems. The reason of the much greater stability of 1 to water relative to 6 is not yet clear; a crystallographic investigation is in progress: D. D. DesMarteau, W. T. Pennington, and V. Montanari, J. Mol. Struct., in press.
4. 2 in place of triflic acid, but 1 requires more strictly anhydrous conditions until workup. Compound 1 extends the reactions of 6 to aqueous systems. The reason of the much greater stability of 1 to water relative to 6 is not yet clear; a crystallographic investigation is in progress: D. D. DesMarteau, W. T. Pennington, and V. Montanari, J. Mol. Struct., in press.
5. 2 in place of triflic acid, but 1 requires more strictly anhydrous conditions until workup. Compound 1 extends the reactions of 6 to aqueous systems. The reason of the much greater stability of 1 to water relative to 6 is not yet clear; a crystallographic investigation is in progress: D. D. DesMarteau, W. T. Pennington, and V. Montanari, J. Mol. Struct., in press.
6. "Chemistry and Biochemistry of the Amino Acids," ed. by G. C. Barrett, Chapman and Hall, London (1985); "The Peptides: Analysis, Synthesis, Biology,"ed. by E. Gross and J. Meienhofer, Academic Press, London (1979), Vol. 1.
7. "Chemistry and Biochemistry of the Amino Acids," ed. by G. C. Barrett, Chapman and Hall, London (1985); "The Peptides: Analysis, Synthesis, Biology,"ed. by E. Gross and J. Meienhofer, Academic Press, London (1979), Vol. 1.
8. 2 phase was separated and washed with 3 × 100 mL water. It was then stirred at 20 °C with 2 × 150 mL 6M HCl for 3 h. The combined acid solutions were dried to constant weight, yielding 2.30 g (77%) of crystalline 4a hydrochloride monohydrate, mp 159-160 °C. Similarly were prepared 4b hydrochloride (78%), mp 203-204 °C, and 4c (95%), mp 166-167 °C. The composition of 4a-c was established by the correct elemental analyses of the bulk products.
9. 4, evaporating, and pumping at 0.05 mmHg gave 5a (158 mg, 95%) as a white powder, mp 73-76 °C.
10. L. A. Carpino, J. Org. Chem., 53, 875 (1988); J. Coste, E. Frerot, and P. Jouin, J. Org. Chem., 59, 2437 (1994); S. Nozaki, Chem. Lett., 1997, 1.
11. L. A. Carpino, J. Org. Chem., 53, 875 (1988); J. Coste, E. Frerot, and P. Jouin, J. Org. Chem., 59, 2437 (1994); S. Nozaki, Chem. Lett., 1997, 1.
12. L. A. Carpino, J. Org. Chem., 53, 875 (1988); J. Coste, E. Frerot, and P. Jouin, J. Org. Chem., 59, 2437 (1994); S. Nozaki, Chem. Lett., 1997, 1.
13. Y. Tamura, F. Watanabe, T. Nakatani, K. Yasui, M. Fuji, T. Komurasaki, H. Tsuzuki, R. Maekawa, T. Yoshioka, K. Kawada, K. Sugita, and M. Ohtani, J. Med. Chem., 41, 640 (1998).
14. M. Steinman, J. G. Topliss, R. Alekel, Y-S Wong, and E. E. York, J. Med. Chem., 16, 1354 (1973); E. H. Banitt, W. R. Bronn, W. E. Coyne, and J. R. Schmid, J. Med. Chem., 20, 821 (1977).
15. M. Steinman, J. G. Topliss, R. Alekel, Y-S Wong, and E. E. York, J. Med. Chem., 16, 1354 (1973); E. H. Banitt, W. R. Bronn, W. E. Coyne, and J. R. Schmid, J. Med. Chem., 20, 821 (1977).
16. Details on the in vitro anticancer testing protocols are available at http://dtp.nci.nih.gov.