TY - JOUR
T1 - Hydrolytic enzymatic transformation of advanced synthetic intermediates
T2 - On the choice of the organic cosolvent
AU - Berkowitz, David B.
AU - Hartung, Ryan E.
AU - Choi, Sungjo
N1 - Funding Information:
Financial support from the American Cancer Society (RPG-96-001-03-CDD) is gratefully acknowledged. D.B.B. is an Alfred P. Sloan Research Fellow (1997–2001). R.E.H. thanks the University of Nebraska for a SURE undergraduate research fellowship through a grant from the Howard Hughes Medical Institute. We thank Mohua Bose for assistance with kinetics fitting programs, and Dr. Richard K. Shoemaker for assistance with NMR experiments. This research was facilitated by grants for NMR and GC/MS instrumentation from the NIH (SIG 1-S10-RR06301), and the NSF (CHE-93000831), respectively.
PY - 1999/12/3
Y1 - 1999/12/3
N2 - For enzymatic hydrolyses of advanced synthetic intermediates, the use of an organic cosolvent is often warranted. As a model study, the cosolvent dependence (at 10 volume%) of the key enzymatic step in our asymmetric synthesis of (-)-podophyllotoxin was examined. At high protein concentrations and rt, DMSO and the polyethereal organic cosolvents dioxane, diglyme and triglyme emerged as the best organic cosolvents, in terms of yield, % ee and catalytic efficiency (V(max)/K(m)). However, only in 10% triglyme was optimal efficiency maintained at both lower protein concentration and higher temperature. (C) 1999 Elsevier Science Ltd.
AB - For enzymatic hydrolyses of advanced synthetic intermediates, the use of an organic cosolvent is often warranted. As a model study, the cosolvent dependence (at 10 volume%) of the key enzymatic step in our asymmetric synthesis of (-)-podophyllotoxin was examined. At high protein concentrations and rt, DMSO and the polyethereal organic cosolvents dioxane, diglyme and triglyme emerged as the best organic cosolvents, in terms of yield, % ee and catalytic efficiency (V(max)/K(m)). However, only in 10% triglyme was optimal efficiency maintained at both lower protein concentration and higher temperature. (C) 1999 Elsevier Science Ltd.
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U2 - 10.1016/S0957-4166(99)00509-1
DO - 10.1016/S0957-4166(99)00509-1
M3 - Article
AN - SCOPUS:0033399646
SN - 0957-4166
VL - 10
SP - 4513
EP - 4520
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 23
ER -