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神经酰胺转运抑制剂HPA-12的化学酶法合成

A chemoenzymatic synthesis of ceramide trafficking inhibitor HPA-12.

作者信息

Kanojia Seema V, Chatterjee Sucheta, Chattopadhyay Subrata, Goswami Dibakar

机构信息

Bio-Organic Division, Bhabha Atomic Research Centre, Mumbai 400 085, India.

Homi Bhabha National Institute, Training School Complex, Anushakti Nagar, Mumbai 400 094, India.

出版信息

Beilstein J Org Chem. 2019 Feb 18;15:490-496. doi: 10.3762/bjoc.15.42. eCollection 2019.

DOI:10.3762/bjoc.15.42
PMID:30873232
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6404422/
Abstract

A chemoenzymatic synthesis of the title compound has been developed using an efficient and highly enantioselective lipase-catalyzed acylation in a hydrophobic ionic liquid, [bmim][PF], followed by a diastereoselective asymmetric dihydroxylation as the key steps for incorporating the stereogenic centers. The further conversion to the appropriate intermediates and subsequent acylation with lauric acid furnished the target compound.

摘要

已开发出一种通过在疏水性离子液体[bmim][PF]中进行高效且高度对映选择性的脂肪酶催化酰化反应，随后进行非对映选择性不对称二羟基化反应作为引入立体中心的关键步骤，来实现标题化合物的化学酶法合成。进一步转化为合适的中间体并随后用月桂酸进行酰化反应得到了目标化合物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f513/6404422/bbb09f4f4d58/Beilstein_J_Org_Chem-15-490-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f513/6404422/4014b1eaac92/Beilstein_J_Org_Chem-15-490-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f513/6404422/ee39a267d9b0/Beilstein_J_Org_Chem-15-490-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f513/6404422/a9513f2cfa3e/Beilstein_J_Org_Chem-15-490-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f513/6404422/81858f5d7e4d/Beilstein_J_Org_Chem-15-490-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f513/6404422/bbb09f4f4d58/Beilstein_J_Org_Chem-15-490-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f513/6404422/4014b1eaac92/Beilstein_J_Org_Chem-15-490-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f513/6404422/ee39a267d9b0/Beilstein_J_Org_Chem-15-490-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f513/6404422/a9513f2cfa3e/Beilstein_J_Org_Chem-15-490-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f513/6404422/81858f5d7e4d/Beilstein_J_Org_Chem-15-490-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f513/6404422/bbb09f4f4d58/Beilstein_J_Org_Chem-15-490-g006.jpg

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