An Improved Chemo-Enzymatic Synthesis of 1-beta-O-Acyl Glucuronides: Highly Chemoselective Enzymatic Removal of Protecting Groups from Corresponding Methyl Acetyl Derivatives.

An Improved Chemo-Enzymatic Synthesis of 1-beta-O-Acyl Glucuronides: Highly Chemoselective Enzymatic Removal of Protecting Groups from Corresponding Methyl Acetyl Derivatives. Research Abstract Details 

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An Improved Chemo-Enzymatic Synthesis of 1-beta-O-Acyl Glucuronides: Highly Chemoselective Enzymatic Removal of Protecting Groups from Corresponding Methyl Acetyl Derivatives. Abstract Text:

Akiko Baba,Tadao Yoshioka,Akiko Baba,Tadao Yoshioka,Akiko Baba,Tadao Yoshioka,

An improved and widely applicable chemo-enzymatic method for the synthesis of a series of 1-beta-O-acyl glucuronides 5a-f has been developed from the corresponding methyl acetyl derivatives 3a-f, which were stereospecifically synthesized from cesium salts of carboxylic acids 1a-f and methyl 2,3,4-tri-O-acetyl-1-bromo-1-deoxy-alpha-d-glucopyranuronate (2). Chemoselectivity of lipase AS Amano (LAS) in the hydrolytic removal of O-acetyl groups of 3a-f to provide methyl esters 4a-f was influenced by the nature of their 1-beta-O-acyl groups; high selectivity was evident only for 3b and 3f. Carboxylesterase from Streptomyces rochei (CSR), newly screened as an alternative to LAS, showed much greater chemoselectivity toward the O-acetyl groups than LAS; 3a, 3d, and 3e were chemoselectively hydrolyzed only by CSR. The combination of CSR with LAS yielded better results in the hydrolysis of 3c and 3f than did single usage of CSR. Final deprotection of the methyl ester groups of 4a-f to provide 5a-f was chemoselectively achieved by using lipase from Candida antarctica type B (CAL-B) as well as esterase from porcine liver (PLE), although CAL-B possessed higher chemoselectivity and catalytic efficiency than did PLE. CSR also exhibited high chemoselectivity in the synthesis of (S)-naproxen 1-beta-O-acyl glucopyranoside (7) from its 2,3,4,6-tetra-O-acetyl derivative 6.

An Improved Chemo-Enzymatic Synthesis of 1-beta-O-Acyl Glucuronides: Highly Chemoselective Enzymatic Removal of Protecting Groups from Corresponding Methyl Acetyl Derivatives. Publishing Authors By Initials

A Baba,T Yoshioka,A Baba,T Yoshioka,A Baba,T Yoshioka,

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An Improved Chemo-Enzymatic Synthesis of 1-beta-O-Acyl Glucuronides: Highly Chemoselective Enzymatic Removal of Protecting Groups from Corresponding Methyl Acetyl Derivatives. Journal Published:

PUBLICATION TYPE: Journal Article

Journal: The Journal of organic chemistry

VOLUME: 72

Page Numbers: 9541-9

Journal Abbreviation: J. Org. Chem.

ISSN: 0022-3263

DAY: 7

MONTH: 11

YEAR: 2007

An Improved Chemo-Enzymatic Synthesis of 1-beta-O-Acyl Glucuronides: Highly Chemoselective Enzymatic Removal of Protecting Groups from Corresponding Methyl Acetyl Derivatives. Information

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LANGUAGE: eng

NlmUniqueID: 2985193

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AFFILIATION: Hokkaido Pharmaceutical University School of Pharmacy, 7-1 Katsuraoka-cho, Otaru, 047-0264, Hokkaido, Japan.

Country: United States

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MEDLINETA: J Org Chem

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