Studies on development of disulfide bond forming reaction and the application to regioselective disulfide formation

Yakugaku Zasshi

Volumn 116, Issue 6, 1996, Pages 441-456

  Akaji, Kenichi ^a  

^a KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

disulfide bond; endothelin; human insulin; natriuretic peptide; peptide synthesis; silyl chloride

Indexed keywords

ATRIAL NATRIURETIC FACTOR; INSULIN;

AMINO ACID ANALYSIS; CHEMICAL REACTION; DISULFIDE BOND; DRUG SYNTHESIS; HORMONE DETERMINATION; HORMONE STRUCTURE; INSULIN SYNTHESIS; REVIEW; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0030007787     PISSN: 00316903     EISSN: None     Source Type: Journal    
DOI: 10.1248/yakushi1947.116.6_441     Document Type: Review

References (25)

1. Hiskey R. G., "The Peptides," Vol. 3, eds. by Gross E., Meienhofer J., Academic Press, New York, 1981, p. 137; Tam J. P., Su C-R., Liu W., Zhang J-W., J. Am. Chem. Soc., 113, 6657 (1991).
2. Hiskey R. G., "The Peptides," Vol. 3, eds. by Gross E., Meienhofer J., Academic Press, New York, 1981, p. 137; Tam J. P., Su C-R., Liu W., Zhang J-W., J. Am. Chem. Soc., 113, 6657 (1991).
3. Munson M. C., Barany G., J. Am. Chem. Soc., 115, 10203 (1993); Ponsati B., Giralt E., Andreu D., Tetrahedron, 46, 8255 (1990).
4. Munson M. C., Barany G., J. Am. Chem. Soc., 115, 10203 (1993); Ponsati B., Giralt E., Andreu D., Tetrahedron, 46, 8255 (1990).
5. Kamber B., Hartmann A., Eisler K., Riniker B., Rink H., Sieber P., Rittel W., Helv. Chim. Acta, 63, 899 (1980).
6. Numata T., Togo H., Oae S., Chem. Lett., 1979, 329.
7. Kuno S., Akaji K., Ikemura O., Moriga M., Aono M., Mizuta K., Takagi A., Yajima H., Chem. Pharm. Bull., 34, 2462 (1986).
8. Akaji K., Tatsumi T., Yoshida M., Kimura T., Fujiwara Y., Kiso Y., J. Am. Chem. Soc., 114, 4137 (1992).
9. Kambayashi Y., Nakao K., Itoh H., Hosoda K., Saito Y., Yamada T., Mukoyama M., Arai H., Shirakami G., Suga S., Ogawa Y., Jougasaki M., Minamino N., Kangawa K., Matsuo H., Inoue K., Imura H., Biochem. Biophys. Res. Commun., 163, 233 (1989).
10. Atherton E., Sheppard R. C., "The Peptides," Vol. 9, eds. by Udenfriend S., Meienhofer J. H., Academic Press, New York, 1987, p. 1.
11. Kiso Y., Yoshida M., Fujiwara Y., Kimura T., Shimokura M., Akaji K., Chem. Pharm. Bull., 38, 673 (1990).
12. Akaji K., Yoshida M., Tatsumi T., Kimura T., Fujiwara Y., Kiso Y., J. Chem. Soc., Chem. Commun., 1990, 288.
13. Akaji K., Nakagawa Y., Fujiwara Y., Fujino K., Kiso Y., Chem. Pharm. Bull., 41, 1244 (1993).
14. Kangawa K., Fukuda A., Matsuo H., Nature (London), 313, 397 (1985).
15. Zervas L., Photaki I., J. Am. Chem. Soc., 84, 3887 (1962).
16. Veber D. F., Milkowski J. D., Varga S. L., Denkewalter R. G., Hirschmann R. J., J. Am. Chem. Soc., 94, 5456 (1972).
17. Grasseti D. R., Murray J. F., Jr., Arch. Biochem. Biophys., 119, 41 (1967).
18. Akaji K., Fujino K., Tatsumi T., Kiso Y., Tetrahedron Lett., 33, 1073 (1992).
19. Yanagisawa M., Kurihara H., Kimura S., Tomobe Y., Kobayashi M., Mitsui Y., Yazaki Y., Goto K., Masaki T., Nature (London), 322, 411 (1988).
20. Kumagaye S., Kuroda H., Nakajima K., Watanabe T., Kimura T., Masaki T., Sakakibara S., Int. J. Peptide Protein Res., 32, 519 (1988).
21. McCurdy S. N., Pept. Res., 2, 147 (1989).
22. Previero A., Coletti-Previero M. A., Cavadore J-C., Biochim. Biophys. Acta, 147, 453 (1967).
23. Akaji K., Nishiuchi H., Kiso Y., Tetrahedron Lett., 36, 1875 (1995).
24. Sieber P., Kamber B., Hartmann A., Jöhl A., Riniker B., Rittel W., Helv. Chim. Acta, 60, 27 (1977).
25. Akaji K., Fujino K., Tatsumi T., Kiso Y., J. Am. Chem. Soc., 115, 11384 (1993).