Search for new synthetic immunosuppressants II. Tetrazole analogues of hymenistatin I.

• Authors: Paweł Zubrzak , Karol Kociołek , Marek Smoluch , Jerzy Silberring , Marek L Kowalski , Barbara Szkudlińska , Janusz Zabrocki
• Languages of publication: EN

Abstracts

EN

Linear and cyclic hymenistatin I (HS I) analogues with dipeptide segments Ile2-Pro3, Pro3-Pro4 and Val6-Pro7 replaced by their tetrazole analogues Ile-Ψ[CN4]-Ala3, Pro3-Ψ[CN4]-Ala4 and Val6-Ψ[CN4]-Alawere synthesized by the solid phase peptide synthesis method and cyclized with the TBTU and/or HATU reagent. The peptides were examined for their immunosuppressive activity in the lymphocyte proliferation test (LPT).

Keywords

EN

immunosuppression   cis-amide bond   1,5-disubstituted tetrazole ring   hymenistatin I  

• Publisher: Polish Biochemical Society
• Journal: Acta Biochimica Polonica
• Year: 2001
• Volume: 48
• Issue: 4
• Pages: 1151-1154

Dates

published

2001

received

2001-09-19

accepted

2001-12-7

References

• 1. Ellis, G. & West, G.B. (1988) Prog. Med. Chem. 25, 1-33
• 2. Sigal, N.H. & Dumont, F.J. (1992) Annu. Rev. Immunol. 10, 519-560.
• 3. Petit, G.R., Clewlow, P.J., Defresne, C., Doubeck, D.L., Cerny, R.L. & Rutzler, K. (1990) Can. J.Chem. 68, 708-711
• 4. Cebrat, M., Wieczorek, Z. & Siemion, I.Z. (1996) Peptides 17, 191-196.
• 5. Konat, R.K., Mierke, D.F., Kessler, H., Kutscher, B., Bernd, M. & Voegeli, R. (1993) Helv. Chim. Acta76, 1649-1666
• 6. Marshall, G.R., Humblet, C., Van Opdenbosch, N. & Zabrocki, J. (1981) in: Peptides: Synthesis,Structure and Function, Proc. 7th Am. Pept. Symp. (Rich, D. & Gross, E., eds.) pp. 669-672, PierceChemical Co., Rockford IL
• 7. Yu, K.L. & Johnson, R.L. (1987) J. Org. Chem. 52, 2051-2059.
• 8. Zabrocki, J., Smith, G. D., Dunbar, J.B., Jr., Iijima, H. & Marshall, G.R. (1988) J. Am. Chem. Soc. 110, 5875-5880.
• 9. Zabrocki, J., Dunbar, J.B., Jr., Marshall, K.W., Toth, M.V. & Marshall, G.R. (1992) J. Org. Chem. 57, 202-209.
• 10. Smith, G.D., Zabrocki, J., Flak, T.A. & Marshall, G.R. (1991) Int. J. Pept. Protein Res. 37, 191-197.