Condensation of Cys(Acm)-containing peptide segments with silver chloride as an activator of peptide thioesters

Chemistry Letters

Volumn , Issue 11, 1997, Pages 1157-1158

  Kawakami, Toru ^a   Aimoto, Saburo ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0031322704     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.1157     Document Type: Article

References (14)

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2. H. Hojo and S. Aimoto, Bull. Chem. Soc. Jpn., 64, 111 (1991). H. Hojo and S. Aimoto. Bull. Chem. Soc. Jpn., 65, 3055 (1992). H. Hojo, Y. Kwon, Y. Kakuta, S. Tsuda, I. Tanaka, K. Hikichi, and S. Aimoto, Bull. Chem. Soc. Jpn., 66, 2700 (1993). H. Hojo and S. Aimoto, Bull. Chem. Soc. Jpn., 66, 3004 (1993). Y. Kwon, R. Zhang, M. P. Bemquerer, M. Tominaga, H. Hojo, and S. Aimoto, Chem. Lett., 1993, 881. H. Hojo, S. Yoshimura, M. Go, and S. Aimoto, Bull. Chem. Soc. Jpn., 68, 330 (1995).
3. H. Hojo and S. Aimoto, Bull. Chem. Soc. Jpn., 64, 111 (1991). H. Hojo and S. Aimoto. Bull. Chem. Soc. Jpn., 65, 3055 (1992). H. Hojo, Y. Kwon, Y. Kakuta, S. Tsuda, I. Tanaka, K. Hikichi, and S. Aimoto, Bull. Chem. Soc. Jpn., 66, 2700 (1993). H. Hojo and S. Aimoto, Bull. Chem. Soc. Jpn., 66, 3004 (1993). Y. Kwon, R. Zhang, M. P. Bemquerer, M. Tominaga, H. Hojo, and S. Aimoto, Chem. Lett., 1993, 881. H. Hojo, S. Yoshimura, M. Go, and S. Aimoto, Bull. Chem. Soc. Jpn., 68, 330 (1995).
4. H. Hojo and S. Aimoto, Bull. Chem. Soc. Jpn., 64, 111 (1991). H. Hojo and S. Aimoto. Bull. Chem. Soc. Jpn., 65, 3055 (1992). H. Hojo, Y. Kwon, Y. Kakuta, S. Tsuda, I. Tanaka, K. Hikichi, and S. Aimoto, Bull. Chem. Soc. Jpn., 66, 2700 (1993). H. Hojo and S. Aimoto, Bull. Chem. Soc. Jpn., 66, 3004 (1993). Y. Kwon, R. Zhang, M. P. Bemquerer, M. Tominaga, H. Hojo, and S. Aimoto, Chem. Lett., 1993, 881. H. Hojo, S. Yoshimura, M. Go, and S. Aimoto, Bull. Chem. Soc. Jpn., 68, 330 (1995).
5. H. Hojo and S. Aimoto, Bull. Chem. Soc. Jpn., 64, 111 (1991). H. Hojo and S. Aimoto. Bull. Chem. Soc. Jpn., 65, 3055 (1992). H. Hojo, Y. Kwon, Y. Kakuta, S. Tsuda, I. Tanaka, K. Hikichi, and S. Aimoto, Bull. Chem. Soc. Jpn., 66, 2700 (1993). H. Hojo and S. Aimoto, Bull. Chem. Soc. Jpn., 66, 3004 (1993). Y. Kwon, R. Zhang, M. P. Bemquerer, M. Tominaga, H. Hojo, and S. Aimoto, Chem. Lett., 1993, 881. H. Hojo, S. Yoshimura, M. Go, and S. Aimoto, Bull. Chem. Soc. Jpn., 68, 330 (1995).
6. H. Hojo and S. Aimoto, Bull. Chem. Soc. Jpn., 64, 111 (1991). H. Hojo and S. Aimoto. Bull. Chem. Soc. Jpn., 65, 3055 (1992). H. Hojo, Y. Kwon, Y. Kakuta, S. Tsuda, I. Tanaka, K. Hikichi, and S. Aimoto, Bull. Chem. Soc. Jpn., 66, 2700 (1993). H. Hojo and S. Aimoto, Bull. Chem. Soc. Jpn., 66, 3004 (1993). Y. Kwon, R. Zhang, M. P. Bemquerer, M. Tominaga, H. Hojo, and S. Aimoto, Chem. Lett., 1993, 881. H. Hojo, S. Yoshimura, M. Go, and S. Aimoto, Bull. Chem. Soc. Jpn., 68, 330 (1995).
7. T. Kawakami, S. Kogure, and S. Aimoto, Bull. Chem. Soc. Jpn., 69, 3331 (1996).
8. K. White, M. E. Grether, J. M. Abrams, L. Young, K. Farrell, and H. Steller, Science, 264, 677-683 (1994).
9. 18ARII (4.6 × 250 mm) (Nacalai tesque, Kyoto) using an increasing linear gradient of acetonitrile in 0.1% aqueous trifluoroacetic acid. Mass numbers were determined by a Voyager™ DE (PerSeptive Biosystems, Inc., Framingham, MA) using α-cyano-4-hydroxycinnamic acid as a matrix.
10. +, 1357.6.
11. When silver nitrate was used, the desired product 4 was obtained in 28% yield, and the des-Acm product 5 was in 15% after isolation by RP-HPLC. When silver chloride was used, the desired product 4 was obtained in 56% yield after isolation by RP-HPLC.
12. Silver nitrate dissolves completely in DMSO at these condensations. The solubility of the silver chloride was measured in DMSO at room temperature and found to be less than 0.3 mg/mL.
13. +, 1353.4.
14. +, 1367.6.