Burst kinetics and turnover in an esterase mimic

Tetrahedron Letters

Volumn 40, Issue 17, 1999, Pages 3335-3338

  Breslow, Ronald ^a   Nesnas, Nasri ^a  

^a Columbia University ^*  (United States)

Author keywords

Cyclodextrin; Oxime; Zinc

Indexed keywords

CYCLODEXTRIN; ESTERASE; OXIME; ZINC; ZINC COMPLEX;

ACYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION KINETICS; DEACYLATION; HYDROLYSIS; MOLECULAR MODEL; REACTION ANALYSIS;

EID: 0033597146     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00460-8     Document Type: Article

References (10)

1. 1. Breslow, R.; Chipman, D. J. Am. Chem. Soc. 1965, 87, 4195.
2. 2. Breslow, R.; Overman, L. E. J. Am. Chem. Soc. 1970, 92, 1075.
3. 3. Zhang, B.; Breslow, R. J. Am. Chem. Soc. 1997, 119, 1676.
4. 6, 300 MHz): δ 10.3 (s, 1H, CH aldehyde), 8.9 (s, 1H, CH oxime), 8.8 (d, 1H, phen Ar), 8.6 (d, 1H, phen Ar), 8.3 (d, 1H, phen Ar), 8.2 (d, 2H, phen Ar), 8.1 (d, 1H, phen Ar), 7.8 (m, 4 H, Ph), 7.45 (m, 6H, Ph), 1.2 (s, 9H, t-Bu). MS (CI) : 490 (M+1) 507 (M+18)
5. 5. Fujita, K.; Tahara, T.; Imoto, T.; Koga, T. J. Am. Chem. Soc. 1986, 108, 2030.
6. 6. Yuan, D.-Q.; Fujita, K.; Ohta, K. Chem. Commun. 1996, 821.
7. 6, 300 MHz): δ 8.0 (s, 1H, CH oxime), 7.8-8.6 (m, 6H, phen Ar), 5.5-6.5 (m, 13H, 2° CD-OH), 4.7-5.0 (m, 7H, CD anomeric), 4.3-4.6 (m, 7H, CD 1°OH), 3.5-4.0 (m, 28H, CD), 3.0-3.5 (m, 14+, CD+dmso). MS (FAB) : 1370 (M+1)
8. 6 (6-HOAc), 400 MHz): δ 11.9 (s, 1H, =NOH oxime), 8.55 (d, 2H, phen Ar), 8.5 (s, 1H, CH oxime), 8.2 (d, 1H, phen Ar), 8.0 (m, 2H, phen Ar), 7.9 (d, 1H, phen Ar), 5.6-5.9 (m, 14H, 2° CD-OH), 4.7-5.0 (m, 7H, CD anomeric), 4.0-4.5 (m, 6H, CD 1°OH), 3.5-4.0 (m, 28H, CD), 3.0-3.5 (m, 14+, CD+dmso), 1.9 (s, HOAc). MS (FAB) : 1370 (M+1)
9. 9. Hartley, B. S.; Kilby, B. A. Biochem. J. 1954, 56, 294.
10. 10. Breslow, R.; Dong, S. D. Chem. Rev. 1998, 98, 1997-2011.