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本文引用的文献

1
Incorporation of tritium from [(4R)-4-3H]mevalonate into abscisic acid.将[(4R)-4-³H]甲羟戊酸中的氚掺入脱落酸。
Biochem J. 1969 Aug;113(5):895-7. doi: 10.1042/bj1130895.
2
Stereospecificity of isopentenylpyrophosphate isomerase and prenyl transferase from pinus and citrus.来自松树和柑橘的异戊烯基焦磷酸异构酶和异戊二烯基转移酶的立体特异性。
Arch Biochem Biophys. 1972 Oct;152(2):590-6. doi: 10.1016/0003-9861(72)90254-8.
3
Studies on the biosynthesis of cholesterol XIX. Steric course of hydrogen eliminations and of C-C bond formations in squalene biosynthesis.胆固醇生物合成的研究 XIX. 角鲨烯生物合成中氢消除和碳-碳键形成的立体化学过程。
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4
Studies on the biosynthesis of cholesterol. 18. The stereospecificity of mevaldate reductase and the biosynthesis of asymmetrically labelled farnesyl pyrophosphate.胆固醇生物合成的研究。18. 甲羟戊酸还原酶的立体特异性及不对称标记法呢基焦磷酸的生物合成。
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Preparative-scale synthesis of (1R)-and (1S)-monodeuteriopropanol by enzymatic exchange reactions.通过酶促交换反应制备规模合成(1R)-和(1S)-单氘代丙醇。
Angew Chem Int Ed Engl. 1973 Feb;12(2):146-7. doi: 10.1002/anie.197301461.
6
Biosynthesis of geraniol and nerol and beta-D-glucosides in Pelargonium graveolens and Rosa dilecta.香叶天竺葵和重瓣玫瑰中香叶醇、橙花醇及β-D-葡萄糖苷的生物合成
Biochem J. 1972 Dec;130(4):1045-54. doi: 10.1042/bj1301045.
7
Biochemical synthesis of stereospecifically hydrogen labelled compounds on a preparative scale, V1-3. Preparation of (1R) (1-2H)- and (1S) (1-2H)-alcohols by exchange reactions catatyzed by yeast or a coupled enzyme system.立体特异性氢标记化合物的制备规模生化合成,V1 - 3。通过酵母或偶联酶系统催化的交换反应制备(1R)(1 - 2H)-和(1S)(1 - 2H)-醇。
Z Naturforsch C. 1973 May-Jun;28(5):241-6.

穿心莲组织培养物中可溶性酶催化反,反-和顺,反-法尼醇的生物合成。

Biosynthesis of trans, trans- and cis, trans-farnesols by soluble enzymes from tissue cultures of Andrographis paniculata.

作者信息

Overton K H, Roberts F M

出版信息

Biochem J. 1974 Dec;144(3):585-92. doi: 10.1042/bj1440585.

DOI:10.1042/bj1440585
PMID:4468823
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC1168537/
Abstract

A cell-free system obtained from tissue cultures of Andrographis paniculata produces 2-trans,6-trans-farnesol (trans,trans-farnesol) and 2-cis,6-trans-farnesol (cis,trans-farnesol) (5:1), incorporating 10% of the radioactivity from 3R-[2-(14)C]mevalonate. There is total loss of (3)H from 3RS-[2-(14)C,(4S)-4-(3)H(1)]mevalonate and total retention from the (4R) isomer in both the trans,trans-farnesol and cis,trans-farnesol formed. When 3RS-[2-(14)C,5-(3)H(2)]mevalonate is used as substrate, there is total retention of (3)H in the trans,trans-farnesol, but loss of one-sixth of the (3)H in the cis,trans-farnesol. With (1R)- and (1S)-[4,8,12-(14)C(3),1-(3)H(1)]-trans,trans -farnesol and (1R)- and (1S)-[4,8,12-(14)C(3),1-(3)H(1)]-cis, trans-farnesol as substrates, the label is lost from the (1R)-cis,trans and (1S)-trans,trans isomers but retained in the (1R)-trans,trans and (1S)-cis,trans isomers; this shows that the pro-1S hydrogen is exchanged in the conversion of trans,trans-farnesol into cis,trans-farnesol and the pro-1R hydrogen in the conversion of cis,trans-farnesol into trans,trans-farnesol. (1R)-[1-(3)H(1)]-trans,trans-Farnesol and (1R)-[1-(3)H(1)]-cis,trans-farnesol have been synthesized by asymmetric chemical synthesis and exchanged with liver alcohol dehydrogenase. Both the trans- and the cis-alcohol exchange the pro-1R hydrogen atom.

摘要

从穿心莲组织培养物中获得的无细胞体系可产生2-反式,6-反式-金合欢醇(反式,反式-金合欢醇)和2-顺式,6-反式-金合欢醇(顺式,反式-金合欢醇)(比例为5:1),并掺入了3R-[2-(14)C]甲羟戊酸10%的放射性。在形成的反式,反式-金合欢醇和顺式,反式-金合欢醇中,3RS-[2-(14)C,(4S)-4-(3)H(1)]甲羟戊酸中的(3)H完全损失,而(4R)异构体中的(3)H则完全保留。当使用3RS-[2-(14)C,5-(3)H(2)]甲羟戊酸作为底物时,反式,反式-金合欢醇中的(3)H完全保留,但顺式,反式-金合欢醇中的(3)H损失了六分之一。以(1R)-和(1S)-[4,8,12-(14)C(3),1-(3)H(1)]-反式,反式-金合欢醇以及(1R)-和(1S)-[4,8,12-(14)C(3),1-(3)H(1)]-顺式,反式-金合欢醇作为底物时,(1R)-顺式,反式和(1S)-反式,反式异构体中的标记丢失,但(1R)-反式,反式和(1S)-顺式,反式异构体中保留;这表明在反式,反式-金合欢醇转化为顺式,反式-金合欢醇的过程中,1S位的氢发生了交换,而在顺式,反式-金合欢醇转化为反式,反式-金合欢醇的过程中,1R位的氢发生了交换。(1R)-[1-(3)H(1)]-反式,反式-金合欢醇和(1R)-[1-(3)H(1)]-顺式,反式-金合欢醇已通过不对称化学合成法合成,并与肝醇脱氢酶进行了交换。反式醇和顺式醇均交换了1R位的氢原子。