Synthesis of stereoselectively labeled [9-2H,3H]chorismate and the stereochemical course of 5-enolpyruvoylshikimate-3-phosphate synthethase
Synthesis of stereoselectively labeled [9-2H,3H]chorismate and the stereochemical course of 5-enolpyruvoylshikimate-3-phosphate synthethase
复制标题
立体选择性标记[9-2H,3H]分支酸的合成及5-烯醇丙酮酰莽草酸-3-磷酸合成酶的立体化学过程
DOI：
10.1021/ja00321a037
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发表时间：
1984
影响因子：
15
通讯作者：
J. Knowles
中科院分区：
文献类型：
--
作者：
C. Grimshaw;S. Sogo;S. Copley;J. Knowles
二甲基亚砜，室温，12小时;（B）威尔金森催化剂/H2;（C）桦树还原;（d）（S）-乳酸脱氢酶/3-乙酰基吡啶腺嘌呤二核苷酸;（e）Kuhn-Roth氧化。甲基-X亚砜，并在室温下放置12-24小时，直到NMR显示仅存在芳基烯醇醚8.15。然后使用威尔金森催化剂17用顺式立体化学还原该物质，得到两种非对映异构的芳基乳基醚。桦树减少18提供（7？，S）-乳酸酯，其中碳2处的构型与碳3处的构型相关（方案III）。通过用（S）-乳酸盐氧化来去除（F）-乳酸盐
Dimethyl sulfoxide, room temperature, 12 h;(b) Wilkinson’s catalyst/H2;(c) Birch reduction;(d)(S)-lactate dehydrogenase/3-acetylpyridine adenine dinucleotide;(e) Kuhn-Roth oxidation. methyl-X sulfoxide and left at room temperature for 12-24 h, until the NMR showed the presence onlyof the aryl enol ether8.15 This material was then reduced with cis stereochemistry using Wilkinson’s catalyst17 to yield the two diastereoisomeric aryl lactyl ethers. Birch reduction18 afforded (7?, S)-lactate in which the configuration at carbon 2 is related to that at carbon 3 (Scheme III). The (F)-lactate was removed by oxidation with (S)-lactate