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Stereoselective preparation of lipidated carboxymethyl-proline/pipecolic acid derivatives via coupling of engineered crotonases with an alkylmalonyl-CoA synthetase.

机译：通过工程化的巴豆酶与烷基丙二酰辅酶A合成酶的偶联，立体选择性地制备脂质化的羧甲基脯氨酸/哌酸衍生物。

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摘要

The trisubstituted enolate- and C-C bond-forming capacities of engineered carboxymethylproline synthases CMPSs are coupled with the malonyl-CoA synthetase MatB to enable stereoselective preparation of 5- and 6-membered N-heterocycles functionalised with alkyl-substituted carboxymethyl side chains, starting from achiral alkyl-substituted malonic acids and L-amino acid semialdehydes. The results illustrate the biocatalytic utility of crotonases in tandem enzyme-catalysed reactions for stereoselective synthesis.

机译：工程化的羧甲基脯氨酸合酶CMPS的三取代的烯醇盐和CC形成键的能力与丙二酰辅酶A合成酶MatB结合，从而能够从非手性开始立体选择性地制备被烷基取代的羧甲基侧链官能化的5和6元N-杂环烷基取代的丙二酸和L-氨基酸半醛。该结果说明了巴豆酶在串联酶催化的立体选择性合成反应中的生物催化作用。

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Hamed, RB; Henry, L; Gomez-Castellanos, JR; Asghar, A; Brem, J; Claridge, TD; Schofield, CJ;
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年度 2013
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1. Stereoselective preparation of lipidated carboxymethyl-proline/pipecolic acid derivatives via coupling of engineered crotonases with an alkylmalonyl-CoA synthetase [J] . Refaat B. Hamed, Luc Henry, J. Ruben Gomez-Castellanos, Organic & biomolecular chemistry . 2013,第47期

机译：通过工程化巴豆酶与烷基丙二酰辅酶A合成酶的偶联立体选择制备脂化羧甲基脯氨酸/哌酸衍生物
2. Total synthesis of pipecolic acid and 1-C-alkyl 1,5- iminopentitol derivatives by way of stereoselective aldol reactions from (S)-isoserinal [J] . Sebastian Baś, Rafat Kusy, Monika Pasternak-Suder, Organic & biomolecular chemistry . 2018,第7期

机译：通过（S）-异丝氨酸的立体选择性羟醛反应全合成哌啶酸和1-C-烷基1,5-亚氨基戊醇衍生物
3. Stereoselective access to fluorinated and non-fluorinated quaternary piperidines: Synthesis of pipecolic acid and iminosugar derivatives [J] . Fustero S., Albert L., Mateu N., Chemistry: A European journal . 2012,第12期

机译：立体选择氟化和非氟化季哌啶：胡椒酸和亚氨基糖衍生物的合成
4. Straightforward Synthesis of CF3-substituted Triarylethenes via Stereoselective Three-fold Cross-coupling Reaction of 1,1-Dibromo-3,3,3-trifluoro-2-tosyloxypropene with Organoboronic Acids [C] . Youhei Takeda, Masaki Shimizu, Tamejiro Hiyama Symposium on Organometallic Chemistry . 2007

机译：通过用有机硼酸的1,1-二溴-3,3,3-三氟-2-甲硅烷基丙烯的立体选择性三倍的三抗偶联反应直接合成CF3取代的三芳基。
5. Exploration of alpha-Diazocarbonyl Compounds for Transition-Metal Catalyzed Carbon-Carbon Bond Formations. Development of Palladium-Catalyzed Stereoselective Synthesis of Trisubstituted Alkenes and the Synthesis of Quaternary alpha,alpha-Heterodiaryl Carboxylic Acids by Rhodium-Catalyzed Multi-Component Coupling Reactions. [D] . Tsoi, Yuk Tai. 2012

机译：探索用于过渡金属催化的碳-碳键形成的α-重氮羰基化合物。铑催化的多组分偶合反应在钯催化的立体选择性合成三取代的烯烃上的发展和季铵的α，α-杂二芳基羧酸的合成。
6. A Mild Synthesis of Bicyclic Alkoxyoxazolium Salts from Proline and Pipecolic Acid Derivatives [O] . Eleonora Spinozzi, Adriano Bauer, Nuno Maulide -1

机译：从脯氨酸和胡椒酸衍生物轻度合成双环烷恶唑盐。
7. Stereoselective preparations of epoxy-, fluoro- and related derivatives of ricinoleic acid and 13(S)-hydroxyoctadeca-9(Z),11(E)-dienoic acid [O] . Muhammad Nor Bin Omar, Richard J. Hamilton, Humphrey A. Moynihan 2003

机译：蓖麻油酸和13（s） - 羟基十八碳-9（Z），11（E） - 二烯酸的环氧 - ，氟 - 和相关衍生物的立体选择性制剂
8. Stereoselective synthesis of optically active aspartic acid from derivatives of fumaric acid and maleic acid [R] . Harada, K., Matsumoto, K. 1966

机译：从富马酸和马来酸的衍生物立体选择性合成光学活性的天冬氨酸

Stereoselective preparation of lipidated carboxymethyl-proline/pipecolic acid derivatives via coupling of engineered crotonases with an alkylmalonyl-CoA synthetase.

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