Synthesis of trimethyl (2S,3R)- and (2R,3R)-[2-H-2(1)]-homocitrates and dimethyl (2S,3R)- and (2R,3R)-[2-H-2(1)]-homocitrate lactones - an assay for the stereochemical outcome of the reaction catalysed both by homocitrate synthase and by the Nif-V pr

Tavassoli A; Duffy JES; Young DW

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Synthesis of trimethyl (2S,3R)- and (2R,3R)-[2-H-2(1)]-homocitrates and dimethyl (2S,3R)- and (2R,3R)-[2-H-2(1)]-homocitrate lactones - an assay for the stereochemical outcome of the reaction catalysed both by homocitrate synthase and by the Nif-V pr

机译：三甲基（2S，3R）-和（2R，3R）-[2-H-2（1）]-高纯酸酯和二甲基（2S，3R）-和（2R，3R）-[2-H-2（ 1）]-均聚内酯-通过均柠檬酸合酶和Nif-V pr催化催化反应的立体化学结果的方法

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Trimethyl (3R)-homocitrate 17, trimethyl (2S,3R)-[2-(2) H-1]-homocitrate 17a and (2R,3R)-[2-H-2(1)]-homocitrate 17b, as well as dimethyl (3R)-homocitrate lactone 18, (2S,3R)-[2-H-2(1)]-homocitric lactone 18a and (2R,3R)-[2-H-2(1)]-homocitric lactone 18b have been synthesised. D-Quinic acid 12 was used as the source of the (3R)-centre in the unlabelled target compounds 17 and 18. (-)-Shikimic acid 19 and the (-)-[2-H-2]-shikimic acid derivative 32 respectively were used in the synthesis of the labelled compounds. In the latter syntheses, Sharpless directed epoxidation of the olefin in the 5-deoxy ester diols 23 and 35 ensured a reaction from the same face as the allylic and homoallylic alcohols, and the reduction of the protected epoxides 25 and 37 ensured that the label was introduced in a stereoselective manner. The H-1 NMR spectra of the labelled products present an assay for the stereochemistry of the biological reactions catalysed by homocitrate synthase and by the protein from the nifV gene.

机译：三甲基（3R）均聚物17，三甲基（2S，3R）-[2-（2）H-1]均聚物17a和（2R，3R）-[2-H-2（1）]均聚物17b以及（3R）-二甲基内酯18，（2S，3R）-[2-H-2（1）]-内酯18a和（2R，3R）-[2-H-2（1）]-二甲基内酯18b已经合成。 D-奎宁酸12用作未标记目标化合物17和18中（3R）中心的来源。（-）-草酸19和（-）-[2-H-2] -shi草酸衍生物在标记化合物的合成中分别使用了32种。在后者的合成中，5-脱氧酯二醇23和35中烯烃的Sharpless定向环氧化可确保与烯丙基和均烯丙基醇的表面反应相同，并且受保护的环氧化物25和37的还原可确保标记为以立体选择的方式引入。标记产物的H-1 NMR光谱提供了对均柠檬酸合酶和nifV基因蛋白催化的生物反应的立体化学的测定方法。

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来源
《Organic & biomolecular chemistry》 |2006年第3期|p. 569-580|共12页
作者
Tavassoli A; Duffy JES; Young DW;
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作者单位

Univ Sussex, Dept Chem, Brighton BN1 9QJ, E Sussex, England;

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原文格式 PDF
正文语种 eng
中图分类物理化学（理论化学）、化学物理学;
关键词
ENANTIOSPECIFIC SYNTHESIS; LYSINE BIOSYNTHESIS; CITRATE SYNTHASE; D-MANNOSE; ACID; INTERMEDIATE;

机译：对映体合成;赖氨酸生物合成;柠檬酸合酶;D-甘露糖;酸;中间体;

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1. Synthesis of trimethyl(2S,3R)- and(2R,3R)-[2-~2H_1]-homocitrates and the corresponding dimethyl ester lactones-towards elucidating the stereochemistry of the reaction catalysed by homocitrate synthase and by the Nif-V protein [J] . All Tavassoli, James E.S.Duffy, Douglas W.Young Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2005,第12期

机译：三甲基（2S，3R）-和（2R，3R）-[2-〜2H_1]-同酸酯和相应的二甲基酯内酯的合成，从而阐明了由纯柠檬酸合酶和Nif-V蛋白催化的反应的立体化学
2. Synthesis of trimethyl(2S,3R)- and(2R,3R)-[2-~2H_1]-homocitrates and the corresponding dimethyl ester lactones-towards elucidating the stereochemistry of the reaction catalysed by homocitrate synthase and by the Nif-V protein [J] . All Tavassoli, James E.S.Duffy, Douglas W.Young Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2005,第12期

机译：三甲基（2S，3R）-和（2R，3R）-[2-〜2H_1]-同酸酯和相应的二甲基酯内酯的合成，从而阐明了由纯柠檬酸合酶和Nif-V蛋白催化的反应的立体化学
3. Asymmetric conjugate reductions with samarium diiodide: asymmetric synthesis of (2S,3R)- and (2S,3S)[2-H-2,3-H-2]-leucine-(S)-phenylalanine dipeptides and (2S,3R)[2-H-2,3-H-2]-phenylalanine methyl ester [J] . Davies SG, Rodriguez-Sola H, Tamayo JA, Organic & biomolecular chemistry . 2005,第8期

机译：二碘化sa的不对称共轭还原：（2S，3R）-和（2S，3S）[2-H-2,3-H-2]-亮氨酸-（S）-苯丙氨酸二肽和（2S，3R）的不对称合成[2-H-2,3-H-2]-苯丙氨酸甲酯
4. Asymmetric synthesis of fully protected (2S,3R)-N-(1',1'-di-methylallyl)-3-hydroxytryptopahan,a new amino acid found in anti-inflammatory cyclic peptide cyclomarin C [C] . Zhu-Jun Yao, Shi-Jun Wen European Peptide Symposium . 2002

机译：完全保护的不对称合成（2S，3R）-N-（1'，1'-二甲基ally1）-3-羟基特普坦，在抗炎环肽环甘油蛋白C中发现的新氨基酸
5. The asymmetric synthesis of (2S,3R)-capreomycidine and the total synthesis of capreomycin IB. [D] . DeMong, Duane Eugene. 2003

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7. A Novel PCC-Catalyzed Process Involving the Oxidative Cleavage of an α-Bromomethyl-tetrahydrofuran Bond. Synthesis of (2S,3R)-2-{(R)-Bromo[(2R,3R,5S,6R)-3,5-dibromo-6-ethyltetrahydro-2H-pyran-2-yl]methyl}-5-oxotetrahydrofuran-3-yl Benzoate [O] . Vincenzo Piccialli 2017

机译：新型pCC催化的过程涉及α-溴甲基 - 四氢呋喃键的氧化裂解。（2s，3R）-2 - {（R） - 溴[（2R，3R，5s，6R）-3,5-二溴-6-乙基四氢-2H-吡喃-2-基]甲基} -5-的合成氧代四氢呋喃-3-基苯甲酸酯
8. New Thermotropic Chiral Nematic Copolymers Using (1S,2S,3S,5R)-(+)- and(1R,2R,3R,5S)-(-)-Isopinocampheol as Building Blocks [R] . Chen, S. H., Tsai, M. L. 1990

机译：新型热致手性向列型共聚物（1s，2s，3s，5R） - （+） - 和（1R，2R，3R，5s） - （ - ） - Isopinocampheol作为构件

Synthesis of trimethyl (2S,3R)- and (2R,3R)-[2-H-2(1)]-homocitrates and dimethyl (2S,3R)- and (2R,3R)-[2-H-2(1)]-homocitrate lactones - an assay for the stereochemical outcome of the reaction catalysed both by homocitrate synthase and by the Nif-V pr

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