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Abstrakty
N-Boc-_-alkylserines (_-hydroxymethylamino acids) undergo a cyclization reaction without racemization to N-Boc-_-alkylserine-_-lactones in 90-98% yield using Mitsunobu conditions (Ph P, diethyl azodicarboxylate). Treatment of the corresponding _-lactones with sulphur nucleophiles (thiolacetic acid or 4-methoxybenzylmercaptan) gives S-protected N-Boc-_-alkylcysteines (_-mercaptomethylamino acids) in high yield. These chimeric _,_-disubstituted amino acids, being incorporated into peptide chain, are able to close the cyclic structure as a disulfide bond.
Wydawca
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Rocznik
Tom
Strony
831--835
Opis fizyczny
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autor
- Institute of Organic Chemistry, Technical University, 90-924 Łódź, Żeromskiego 116, Poland, olmaola@p.lodz.pl
Bibliografia
- 1. Presented at the XVTI Polish Peptide Symposium, August 31 - September 4,2003, Technical University, Łódź, Poland
- 2. See e.g., Hruby V.J., AI-Obeidi F. and Kazmierski W., Biochem. J., 268, 249 (1990).
- 3. Naegeli H.U. and Zahner H„ Helv. Chim. Acta, 63, 1400 (1980).
- 4. Carmeli S., Moore R.E., Patterson G.M.L., CorbettT.H. and Valeriote F.A., J. Am. Chem. Soc., 112,8195 (1990); Carmeli S., Moore R.E. and Patterson G.M.L., Tetrahedron Lett., 32, 2593 (1991).
- 5. Pattenden G. and Thom S.M., Synlett, 533 (1992).
- 6. Williams R.M., Synthesis of Optically Active a-Amino Acids, Pergamon Press, (1989).
- 7. Pattenden G., Thom S.M and Jones M.F., Tetrahedron, 49, 2131 (1993).
- 8. Shao H., Zhu Q. and Goodman M., J. Org. Chem., 60, 790 (1995).
- 9. Kamiński Z:J., Leplawy M.T. and Zabrocki J., Synthesis, 792 (1973).
- 10. Kamiński Z.J. and Leplawy M.T., Synthesis, 292 (1974).
- 11. Leplawy M.T. and Olma A., Polish J. Chem., 53,354 (1979); Olma A., Polish J. Chem., 70,1442(1996).
- 12. Wieczorek W., Bukowska-Strzyżewska M., Leplawy M.T. and Olma A., J. Crystallogr. Spectrosc. Res., 19,257 (1989); Wieczorek W., Bukowska-Strzyżewska M., Leplawy M.T. and Olma A., J. Crystallogr. Spectrosc. Res., 21,209 (1991); Wieczorek W., Bukowska-Strzyżewska M., Olma A., Kamiński Z.J. and Leplawy M.T., J. Crystallogr. Spectrosc. Res., 21, 107 (1991).
- 13. Witkowska R, Kaczmarek K., Crisma M., Toniolo C. and Zabrocki J., J. Pept. Sci., 7, 619 (2001).
- 14. Olma A., Lachwa M. and Lipkowski A.W., J. Pept. Res., 62,45 (2003).
- 15. Khalil E.M., Subasinghe N.L. and Johnson R.L., Tetrahedron Lett., 37, 3441 (1996).
- 16. Still W.C., Kahn M. and Mitra A., J. Org. Chem., 43, 2923 (1978).
- 17. Wiśniewski K., Kołodziejczyk A.S. and Falkiewicz B., J. Pept. Sci., 4, 1 (1998).
- 18. Rabjohn N., Org. Synth., Coll. Vol. 3, 375 (1955).
- 19. Goodman M., Cai W. and Smith N.D., J. Pept. Sci., 9, 594 (2003).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ1-0024-0031