Chemo-Enzymatic Synthesis of a Multi-Useful Chiral Building Block Molecule for the Synthesis of Medicinal Compounds

Nakano, Toshiki; Yagi, Yusuke; Miyahara, Mizuki; Kaminura, Akio; Kawatsura, Motoi; Itoh, Toshiyuki

doi:10.3390/molecules16086747

Cited by 7 publications

(5 citation statements)

References 25 publications

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“…The dominant method for the preparation of taxol was the semisynthesis route by attaching a synthetic optically active C-13 side chain to natural baccatin III derived from renewable yew leaves. Chemoenzymatic synthesis protocols have been recognized as a very useful means to prepare optically active compounds [14,15]. Lipase-catalyzed asymmetric hydrolysis routes have been widely reported in the chemoenzymatic synthesis of taxol’s C-13 side chain [1].…”

Section: Introductionmentioning

confidence: 99%

Bioresolution Production of (2R,3S)-Ethyl-3-phenylglycidate for Chemoenzymatic Synthesis of the Taxol C-13 Side Chain by Galactomyces geotrichum ZJUTZQ200, a New Epoxide-Hydrolase-Producing Strain

et al. 2014

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Abstract:A newly isolated Galactomyces geotrichum ZJUTZQ200 strain containing an epoxide hydrolase was used to resolve racemic ethyl 3-phenylglycidate (rac-EPG) for producing (2R,3S)-ethyl-3-phenylglycidate ((2R,3S)-EPG). G. geotrichum ZJUTZQ200 was verified to be able to afford high enantioselectivity in whole cell catalyzed synthesis of this chiral phenylglycidate synthon. After the optimization of the enzymatic production and bioresolution conditions, (2R,3S)-EPG was afforded with high enantioselectivity (e.e. S > 99%, E > 49) after a 8 h reaction. The co-solvents, pH buffer solutions and substrate/cell ratio were found to have significant influences on the bioresolution properties of G. geotrichum ZJUTZQ200. Based on the bioresolution product (2R,3S)-EPG, taxol's side chain ethyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropionate was successfully synthesized by a chemoenzymatic route with high enantioselectivity (e.e. S > 95%).

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Section: Introductionmentioning

confidence: 99%

Bioresolution Production of (2R,3S)-Ethyl-3-phenylglycidate for Chemoenzymatic Synthesis of the Taxol C-13 Side Chain by Galactomyces geotrichum ZJUTZQ200, a New Epoxide-Hydrolase-Producing Strain

et al. 2014

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“…The transesterification of alcohols with fatty acid derivatives has been accomplished using lipase PL in various solvents, in which lipase PL possess enzymatic activity in several types of organic solvents including DMF, dioxane, acetone, hexane, and diisopropyl ether . In particular, Mori et al .…”

Section: Resultsmentioning

confidence: 99%

Lipase‐catalyzed synthesis of epigallocatechin gallate‐based polymer for long‐term release of epigallocatechin gallate with antioxidant property

Nitta

Iwamoto

2019

J of Applied Polymer Sci

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Epigallocatechin gallate (EGCG) must be released in a controlled manner in order to maximize its long-term potential as an antioxidant. In this study, lipase-catalyzed polymerization of EGCG with divinyl adipate and sugar alcohols was conducted to form poly-EGCG, which enables long-term controlled release of EGCG via hydrolysis of ester linkages. The polymer yields were influenced by monomer ratios, volume of solvent, and lipase concentration. EGCG was gradually released from polyEGCG under a physiological condition as ester groups of polyEGCG degraded over a period of more than two months, and the releasing rate was influenced by the type of the sugar alcohols and EGCG ratios. EGCG released from polyEGCG maintained its antioxidant activity and the cell viability of polyEGCG eluent with polymer concentration higher than 0.05 mg/mL was as high as 100%. These results indicate that polyEGCG has potential application as a highly efficient and long-term antioxidative material with low cytotoxicity.In this study, we synthesized a new polymer (polyEGCG) consisting of EGCG as a main component, divinyl adipate as a hydrophobic segment, and sugar alcohols as an elongation agent via esterification of divinyl adipate against EGCG and sugar alcohols (Scheme 1). As polyEGCG is introduced into a body transdermally, Additional Supporting Information may be found in the online version of this article.

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“…The methodology enables us to prepare a wide range of allylic nitro compounds in a simple manipulation. Recently, we employed the allylic nitro compounds for the synthesis of FTY-720 derivatives using the Heck reaction . The starting nitro compounds are expected as a potentially useful precursor for the type 2 allylic cascade substitution reaction, because the wide range of the allylic nitro compounds is readily prepared in short steps from nitroalkenes.…”

Section: Introductionmentioning

confidence: 99%

Preparation of 2,3-Dihydrofurans via a Double Allylic Substitution Reaction of Allylic Nitro Compounds

2014

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Chemo-Enzymatic Synthesis of a Multi-Useful Chiral Building Block Molecule for the Synthesis of Medicinal Compounds

Abstract: Optical resolution of 2-methyl-2-nitrobut-3-en-1-ol has been accomplished using a “low-temperature lipase-catalyzed transesterification” carried out at −40 °C.

Cited by 7 publications

References 25 publications

Bioresolution Production of (2R,3S)-Ethyl-3-phenylglycidate for Chemoenzymatic Synthesis of the Taxol C-13 Side Chain by Galactomyces geotrichum ZJUTZQ200, a New Epoxide-Hydrolase-Producing Strain

Bioresolution Production of (2R,3S)-Ethyl-3-phenylglycidate for Chemoenzymatic Synthesis of the Taxol C-13 Side Chain by Galactomyces geotrichum ZJUTZQ200, a New Epoxide-Hydrolase-Producing Strain

Lipase‐catalyzed synthesis of epigallocatechin gallate‐based polymer for long‐term release of epigallocatechin gallate with antioxidant property

Preparation of 2,3-Dihydrofurans via a Double Allylic Substitution Reaction of Allylic Nitro Compounds

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