New synthetic strategy for o-NBS protected amino acids and their use in synthesis of mono-benzylated peptides

Tetrahedron Letters

Volumn 46, Issue 39, 2005, Pages 6637-6640

  De Luca, Stefania ^a   Della Moglie, Raffaella ^a   De Capua, Antonia ^a   Morelli, Giancarlo ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

Building blocks for peptide synthesis; Mono benzylated peptides; o NBS protected amino acids

Indexed keywords

2 NITROBENZENESULFONAMIDE; AMINO ACID DERIVATIVE; BENZENESULFONAMIDE DERIVATIVE; PEPTIDE; UNCLASSIFIED DRUG;

ARTICLE; BENZYLATION; PEPTIDE SYNTHESIS; SOLID PHASE SYNTHESIS;

EID: 23944434415     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.07.154     Document Type: Article

References (18)

1. R. Sandler Organic Functional Group Preparations 2nd ed. 1983 Academic Press New York Chapter 13
2. C.M. Marson, and A.D. Hobson A. Katritzky O. Meth-Cohn C.W. Rees Comprehensive Organic Functional Group Transformation Vol. 2 1995 Pergamon Press Oxford 297
3. T. Fukuyama, C.K. Jow, and M. Cheung Tetrahedron Lett. 36 1995 6373 6374
4. T. Fukuyama, M. Cheung, C.K. Jow, Y. Hidai, and T. Kan Tetrahedron Lett. 38 1997 5831 5834
5. Y. Hidai, T. Kan, and T. Fukuyama Tetrahedron Lett. 40 1999 4711 4714
6. W. Kurosawa, T. Kan, and T. Fukuyama Org. Synth. 79 2002 186 195
7. T. Kan, and T. Fukuyama Chem. Commun. 2004 235 354
8. J.F. Reichwein, and R.M.J. Liskamp Tetrahedron Lett. 39 1998 1243 1246
9. M. Bodanszky, and A. Bodanszky The Practice of Peptide Synthesis 2nd ed. 1994 Springer New York, USA Chapter 2
10. M.L. Di Gioia, A. Leggio, and A. Liguori J. Org. Chem. 70 2005 3892 3897
11. 1H NMR analysis.
12. 1H NMR spectra were recorded on a Varian INOVA-Unity 500 MHz spectrometer. Specific rotation (in deg mL/g dm) is measured by using a Perkin-Elmer model 141 polarimeter.
13. 3OH).
14. The peptides synthesis was carried out by solid phase method using the standard Fmoc procedure. The first amino acid was loaded on Wang resin according to literature protocol (R.C. Sheppard, and B.J. Williams Int. J. Peptide Protein Res. 20 1982 451 454
15. ) and the loading was evaluated by Fmoc test. Amino acid couplings were monitored by Kaiser test (E. Kaiser, R.L. Colescott, C.D. Bossinger, and P.I. Cook Anal. Biochem. 34 1970 595 598 )
16. +), 1220.5; found, m/z 1220.5.
17. +), 294.2; found, m/z 294.6.
18. +), 1364.4; found, m/z 1364.6.