TY - JOUR
T1 - Enzyme-catalyzed asymmetric acylation and hydrolysis of cis-2,5-disubstituted tetrahydrofuran derivatives
T2 - Contribution to development of models for reactions catalyzed by porcine liver esterase and porcine pancreatic lipase
AU - Naemura, Koichiro
AU - Fukuda, Ritsuko
AU - Takahashi, Nobuo
AU - Konishi, Masayoshi
AU - Hirose, Yoshiki
AU - Yoshito, Tobe
PY - 1993/1/1
Y1 - 1993/1/1
N2 - Pig liver esterase, lipase from porcine pancreas, lipase from Pseudomonas sp. (lipase YS), and lipase from Candida cylindracea catalyzed hydrolyses of the cis-diacetate 1 and the trans-diacetate (±)-4 to give the cis-monoacetate 3 and the trans-monoacetate 6 in optically active forms, respectively. Lipase YS-catalyzed acylations of the cis-diol 2 and the trans-diol (±)-5 with an acylating agent in cyclohexane yielded (-)-3 and (-)-6, respectively. The group adjacent to the R stereogenic center preferentially reacted in lipase YS-catalyzed hydrolyses of 1 and (±)-4 and acylations of 2 and (±)-5, and the enantioselectivities are rationalized by our rule recently proposed for lipase YS.
AB - Pig liver esterase, lipase from porcine pancreas, lipase from Pseudomonas sp. (lipase YS), and lipase from Candida cylindracea catalyzed hydrolyses of the cis-diacetate 1 and the trans-diacetate (±)-4 to give the cis-monoacetate 3 and the trans-monoacetate 6 in optically active forms, respectively. Lipase YS-catalyzed acylations of the cis-diol 2 and the trans-diol (±)-5 with an acylating agent in cyclohexane yielded (-)-3 and (-)-6, respectively. The group adjacent to the R stereogenic center preferentially reacted in lipase YS-catalyzed hydrolyses of 1 and (±)-4 and acylations of 2 and (±)-5, and the enantioselectivities are rationalized by our rule recently proposed for lipase YS.
UR - http://www.scopus.com/inward/record.url?scp=0027159502&partnerID=8YFLogxK
U2 - 10.1016/S0957-4166(00)80131-7
DO - 10.1016/S0957-4166(00)80131-7
M3 - Article
AN - SCOPUS:0027159502
VL - 4
SP - 911
EP - 918
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
SN - 0957-4166
IS - 5
ER -