Synthesis of retro-inverso peptides employing isocyanates of Nα-Fmoc-amino acids/peptide acids catalyzed by DMAP

Tetrahedron Letters

Volumn 47, Issue 51, 2006, Pages 9139-9141

  Venkataramanarao, Rao ^a   Sureshbabu, Vommina V ^a  

^a BANGALORE UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; ISOCYANIC ACID DERIVATIVE; PEPTIDE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION KINETICS; CRYSTAL STRUCTURE; PEPTIDE SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 33751107195     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.10.066     Document Type: Article

References (20)

1. Chorev M. Biopolymers 80 (2005) 67-84
2. Chorev M., and Goodman M. Acc. Chem. Res. 26 (1993) 266-273
3. Scheibler L., and Chorev M. Methods of Organic Chemistry, Synthesis of Peptides and Peptidomimetics (2002), Houben-Weyl, New York E 22c, pp 528-550
4. For other protocols for the synthesis of retro-inverso peptides, see Ref. 3.
5. Chorev M., MacDonald S.A., and Goodman M. J. Org. Chem. 49 (1984) 821-827
6. Fletcher M.D., and Campbell M.M. Chem. Rev. 98 (1998) 763-795
7. Sisto A., Verdini A.S., and Virdia A. Synthesis (1985) 294-296
8. Boutin R.H., and Loudon G.M. J. Org. Chem. 49 (1984) 4277-4284
9. Yamamoto Y., Yatagai H., and Maruyama K. J. Org. Chem. 44 (1979) 1746-1747
10. Englund E.A., Gopi H.N., and Appella D.H. Org. Lett. 6 (2004) 213-215
11. Suresh Babu V.V., Ananda K., and Vasanthakumar G.R. J. Chem. Soc., Perkin. Trans. 1 (2000) 4328-4331
12. Vasanthakumar G.R., Ananda K., and Sureshbabu V.V. Indian J. Chem. 41B (2002) 1733-1735
13. Patil B.S., Vasanthakumar G.R., and Suresh Babu V.V. J. Org. Chem. 68 (2003) 7274-7280
14. Patil B.S., and Suresh Babu V.V. Lett. Pept. Sci. 10 (2004) 93-97
15. Gurtler C., and Danielmeier K. Tetrahedron Lett. 45 (2004) 2515-2521
16. Gertzmann R., and Gurtler C. Tetrahedron Lett. 46 (2005) 6659-6662
17. Schuemacher A.C., and Hoffmann R.W. Synthesis (2001) 243-246
18. Ramiah M., and Scriven E.F.V. Aldrichim. Acta 36 (2003) 21-27
19. 4. The solvent was evaporated in vacuo and the residue dissolved in toluene (10 mL) and heated at 90 °C under nitrogen. After 1 h, the solvent was removed under reduced pressure to give the isocyanate, which was used for the next step.
20. 4. The solvent was evaporated and the resulting residue crystallized using ethyl acetate/hexane (2:8).