Penicillin acylase-catalyzed peptide synthesis in aqueous medium: A chemo-enzymatic route to stereoisomerically pure diketopiperazines

Tetrahedron Asymmetry

Volumn 14, Issue 20, 2003, Pages 3123-3128

  Khimiuk, Andrei Y ^a   Korennykh, Alexei V ^a   Van Langen, Luuk M ^b   Van Rantwijk, Fred ^b   Sheldon, Roger A ^b   Švedas, Vytas K ^a  

^a MOSCOW STATE UNIVERSITY   (Russian Federation)

^b DELFT UNIVERSITY OF TECHNOLOGY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

3 (1 METHYLPROPYL) 6 PHENYLPIPERAZINE 2,5 DIONE; 3 (1H IMIDAZOL 4 YLMETHYL) 6 PHENYLPIPERAZINE 2,5 DIONE; 3 (1H INDOL 3 YLMETHYL) 6 PHENYLPIPERAZINE 2,5 DIONE; 3 (2 METHYLPROPYL) 6 PHENYLPIPERAZINE 2,5 DIONE; 3 ISOPROPYL 6 PHENYLPIPERAZINE 2,5 DIONE; 3 METHYL 6 PHENYLPIPERAZINE 2,5 DIONE; 3 PHENYL 2,5 PIPERAZINEDIONE; 3 PHENYL 6 (PHENYLMETHYL)PIPERAZINE 2,5 DIONE; AMINO ACID DERIVATIVE; DIPEPTIDE; PENICILLIN AMIDASE; PIPERAZINE DERIVATIVE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CYCLIZATION; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PEPTIDE SYNTHESIS; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 1642339679     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.08.011     Document Type: Article

References (15)

1. Cheetham P.S.J. Straathof A.J.J., Adlercreutz P. Applied Biocatalysis. 2nd ed. 2000;93-152 Harwood, Amsterdam.
2. Van Langen L.M., Van Rantwijk F., Švedas V.K., Sheldon R.A. Tetrahedron: Asymmetry. 11:2000;1077-1083.
3. Švedas V.K., Savchenko M.V., Beltser A.I., Guranda D.F. Ann. NY Acad. Sci. 799:1996;659-669.
4. Kasche V., Michaelis G., Wiesemann T. Biomed. Biochim. Acta. 50:1991;237-242.
5. Didžiapetris R.J., Švedas V.K. Biomed. Biochim. Acta. 50:1991;5237-5242.
6. Didžiapetris R.J., Drabnig B., Schellenberger V., Jakubke H.-D., Švedas V.K. FEBS Lett. 287:1991;31-33.
7. Reidel A., Waldmann H. J. Pract. Chem. 335:1993;109-127.
8. Shibuya, K. (Ajinomoto), JP 58162260A, 1983.
9. Izumida, H.; Nishijima, M.; Sano, H.; Yamagishi, M.; Oishi, K.; Ota, T.; Motosugi, M.; Kamimura D.; Gotou, M. (Kaiyo Bio. Technol. Kenkyusho), JP 08277203A, 1996.
10. Shimizaki, M.; Henmi, K.; Hashimoto, S. (Fujisawa), JP 63290868A, 1988.
11. Svokos, R. G.; Angier, R. B. (American Cyanamid Co.), US 3560483, 1971.
12. Tanaka K., Mori A., Inoue S. J. Org. Chem. 55:1990;181-185.
13. Danda H. Synlett. 1991;263-264.
14. Kim H.J., Jackson W.R. Tetrahedron: Asymmetry. 5:1994;1541-1548.
15. Shcherbakova T. A.; Korennykh A. V.; Van Langen, L. M.; Van Rantwijk, F. ; Sheldon, R. A.; Švedas, V. K., paper in preparation.