Penicillin G acylase mediated synthesis of the enantiopure (S)-3-amino-azetidinl-2-one

Tetrahedron Asymmetry

Volumn 8, Issue 19, 1997, Pages 3231-3235

  Cainelli, Gianfranco ^a   Giacomini, Daria ^a   Galletti, Paola ^a   DaCol, Marco ^b  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b Biochimica OPOS SpA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 AZETIDINONE DERIVATIVE; 3 AMINO 2 AZETIDINONE DERIVATIVE; AMIDASE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; ENZYME ACTIVITY; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030882447     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00405-9     Document Type: Article

References (12)

1. van der Steen, F. H.; van Koten, G. Tetrahedron 1991, 47, 7503.
2. Stoodley, R. J. in Recent Advances in the Chemistry of β Lactam Antibiotics Elks, J., Ed., The Chemical Society, London, 1977, 190.
3. Duggleby, H. J.; Tolley, S. P.; Hill, C. P.; Dodson, E. J.; Dodson, G.; Moody, P. C. E. Nature 1995, 373, 264.
4. Baldaro, E.; Fuganti, C.; Servi, S.; Tagliani, A.; Terreni, M. in Microbial Reagents in Organic Synthesis Kluwer Academic Publishers, 1992, 175.
5. Briggs, B. S.; Wright, I. G.; Zmijewski, M. J. New J. Chem. 1994, 18, 425.
6. Cainelli; G.; DaCol; M.; Galletti; P.; Giacomini, D. Synlett 1997, 923.
7. The correction factor between NaOH titration and real conversion has been established through a calibration plot and a quantitative HPLC analysis.
8. Cimarusti, C. M.; Applegate, H. E; Chang, H. W.; Floyd, D. M.; Koster, W. H.; Slusarchyk, W. A.; Young, M. G. J. Org. Chem. 1982, 47, 182.
9. Conversion % and e.e.% were determined through chiral HPLC on phenylacetamide derivatives (R) 4c and (5) 5c.
10. Work is in progress in order to understand these results.
11. Chen, C. S.; Fujimoto, Y.; Girdakaus, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294.
12. The enantiomeric ratio E was calculated with the equation reported in Stecher, H.; Faber, K. Synthesis 1997, 1.