Diphenylphosphoryl Azide. A New Convenient Reagent for a Modified Curtins Reaction and for the Peptide Synthesis

Journal of the American Chemical Society

Volumn 94, Issue 17, 1972, Pages 6203-6205

  Shioiri, Takayuki ^a   Ninomiya, Kunihiro ^a   Yamada, Shun Ichi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AZIDE; PEPTIDE; PHOSPHORIC ACID;

ARTICLE; INFRARED RADIATION; SPECTROSCOPY; SYNTHESIS;

AZIDES; INFRARED RAYS; PEPTIDES; PHOSPHORIC ACIDS; SPECTRUM ANALYSIS;

EID: 0015520853     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00772a052     Document Type: Article

References (9)

1. E. Schroder and K. Lübke, “The Peptides,” Vol. I, Academic Press, New York, N. Y., 1965, p 36.
2. H. E. Baumgarten and A. Staklis, J. Amer. Chem. Soc., 87, 1141 (1965).
3. [α]25D –46.7° (c 0.6, ethyl acetate) [lit. [α]26D –50° (c 0.6, ethyl acetate); see E. Baer, J. Maurukas, and D. D. Clarke, Can. J. Chem., 34, 1182 (1956)].
4. C. A. Buchler and D. E. Pearson, “Survey of Organic Syntheses,” Wiley-Interscience, New York, N. Y., 1970, pp 494–503, and references therein.
5. T. Curtius, Chem. Ber., 35, 3226 (1902).
6. For a recent review, see A. Marglin and R. B. Merrifield, Annu. Rev. Biochem., 39, 841 (1970).
7. The product, (Z)-Leu-Leu-Val-Phe-OMe, had [α]2“D –25.2°; see A. Ide, by the azide method had [α]NNNN20OOOOD –25.4°; see A. Ide, K. Shigezane, S. Shigezane, T. Mizoguchi, and S. Saito, Yakugaku Zasshi, 90, 850 (1970).
8. M. W. Williams and G. T. Young, J. Chem. Soc., 881 (1963).
9. M. W. Williams and G. T. Young, J. Chem. Soc., 3701 (1964).