Enantioselective acylation of β-aminoesters using penicillin G acylase in organic solvents

Tetrahedron Letters

Volumn 40, Issue 19, 1999, Pages 3665-3668

  Roche, Didier ^a   Prasad, Kapa ^a   Repic, Oljan ^a  

^a NOVARTIS INSTITUTES FOR BIOMEDICAL RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDASE; BETA AMINO ACID; PENICILLIN G ACYLASE; UNCLASSIFIED DRUG;

ACYLATION; ANALYTIC METHOD; ARTICLE; CATALYSIS; DRUG ISOLATION; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROPHOBICITY; REACTION ANALYSIS;

EID: 0033531990     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00554-7     Document Type: Article

References (13)

1. 1 a) "Enantioselective Synthesis of β-Aminoacids" E. Juaristi, Wiley-VCH 1997;
2. b) E. Juaristi, D. Quintana, J. Escalante, Aldrichimica Acta 1994, 27, 3;
3. c) D. C. Cole, Tetrahedron 1994, 50, 9517-9582.
4. 2 a) M. P. Sibi, J. J. Shay, M. Liu, C. P. Jasperse, J. Am. Chem. Soc. 1998, 120, 6615-6616;
5. b) S. Kobayashi, H. Ishitani, M. Ueno, J. Am. Chem. Soc. 1998, 120, 431-432.
6. 3 G. Cardillo, L. Gentilluci, A. Tolomelli, C. Tomasini, J. Org. Chem. 1998, 63, 2351-2353.
7. 4 ChiroCLEC™-EC was purchased from Altus: 8300 U/g. PGA on Eupergit® C commercialized by Fluka was also used as catalyst and gave comparable results when used at the same concentration.
8. 5 (R)-(+)-t-Butylphenylphosphinothioic acid: R. K. Haynes, R. N. Freeman, C. R. Mitchell, S. C. Vonwiller, J. Org. Chem. 1994, 59, 2919-2921.
9. 6 Prepared according to: K. Eichenberger, C. Egli, Ger. Offen., 2115763 711028.
10. 7 "Enzymes in Synthetic Organic Chemistry" C.-H. Wong, G. M. Whitesides, Pergamon 1994, chapter 1.8, p. 22, and ref. cited therein.
11. 8 Purchased from Aldrich.
12. 9 The racemic compound was prepared by mixing the pure (R) and (S)-enantiomers purchased from Oxford Asymmetry.
13. 4: C 60.24, H 7.16, N 5.85; found: C 59.88, H 7.38, N 5.68.