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On the synthesis of serine and homoserine samples asymmetrically labelled with tritium and deuterium in the hydroxymethylene group.

作者信息

Fuganti C, Ghiringhelli D, Grasselli P

出版信息

Experientia. 1978 Mar 15;34(3):297-8. doi: 10.1007/BF01922993.

DOI:10.1007/BF01922993
PMID:75808
Abstract

(1R) [1-3H, 2H1] 3-Phenylpropanol, the key intermediate in the synthesis of (4R) [4-3H, 2H1] D,L-homoserine and of the (4S)-isomer, is obtained from (1S) [1-2H1] 3-phenylpropanol and (1RS) [1-3H] ethanol upon incubation with yeast alcohol dehydrogenase and NAD+; under similar conditions 2-phenylethanol undergoes very small exchange with [1-2H2] ethanol.

摘要

相似文献

1
On the synthesis of serine and homoserine samples asymmetrically labelled with tritium and deuterium in the hydroxymethylene group.
Experientia. 1978 Mar 15;34(3):297-8. doi: 10.1007/BF01922993.
2
[Studies on the reaction of alcohol dehydrogenases with tritium-labelled substrates. 3. Primary aliphatic alcohols and aldehydes as substrates of liver alcohol dehydrogenase].[醇脱氢酶与氚标记底物反应的研究。3. 伯脂肪醇和醛作为肝脏醇脱氢酶的底物]
Z Naturforsch B. 1968 May;23(5):623-8.
3
Conversion of 3-nitro-1-propanol (miserotoxin aglycone) to cytotoxic acrolein by alcohol dehydrogenase.通过乙醇脱氢酶将3-硝基-1-丙醇（米瑟罗毒素苷元）转化为细胞毒性丙烯醛。
Biochem Pharmacol. 1981 Oct 1;30(19):2719-20. doi: 10.1016/0006-2952(81)90545-1.
4
Primary deuterium and tritium isotope effects upon V/K in the liver alcohol dehydrogenase reaction with ethanol.在肝脏乙醇脱氢酶与乙醇的反应中，初级氘和氚同位素对V/K的影响。
Biochemistry. 1981 Sep 29;20(20):5662-9. doi: 10.1021/bi00523a004.
5
Alteration in the redox balance of yeast leads to allyl alcohol resistance.酵母氧化还原平衡的改变导致对烯丙醇产生抗性。
FEBS Lett. 1980 Sep 22;119(1):105-8. doi: 10.1016/0014-5793(80)81008-8.
6
[Stereochemistry and mechanism of the methanol oxidase from Candida boidinii (author's transl)].[博伊丁假丝酵母甲醇氧化酶的立体化学与作用机制（作者译）]
Hoppe Seylers Z Physiol Chem. 1975 Oct;356(10):1477-84.
7
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.
8
Stereochemistry of the rearrangement of 2-aminoethanol by ethanolamine ammonia-lyase.
Eur J Biochem. 1983 Nov 2;136(2):303-11. doi: 10.1111/j.1432-1033.1983.tb07742.x.
9
Substrate specificity and stereospecificity of alcohol dehydrogenases.醇脱氢酶的底物特异性和立体特异性。
Nature. 1967 Apr 1;214(5083):31-3. doi: 10.1038/214031a0.
10
The subcellular localization of alcohol dehydrogenase activity in baker's yeast.酒精脱氢酶活性在面包酵母中的亚细胞定位。
Biochim Biophys Acta. 1969;191(3):493-501. doi: 10.1016/0005-2744(69)90342-8.

本文引用的文献

1
Cystathionine -synthase. The nature of intramolecular proton shifts in the elimination reaction.胱硫醚 - 合酶。消除反应中分子内质子转移的本质。
J Biol Chem. 1972 Oct 25;247(20):6412-9.
2
Stereochemistry of the tryptophan synthetase reaction.色氨酸合成酶反应的立体化学
J Am Chem Soc. 1974 Mar 6;96(5):1593-5. doi: 10.1021/ja00812a053.
3
Letter: Stereospecific synthesis of isotopically labeled serine at carbon 3 and stereochemical analysis of D-serine dehydrase reaction.信函：3-碳位同位素标记丝氨酸的立体专一性合成及D-丝氨酸脱水酶反应的立体化学分析
J Am Chem Soc. 1976 May 26;98(11):3397-8. doi: 10.1021/ja00427a070.
4
Letter: Stereochemistry and mechanism of reactions catalyzed by tryptophanase and tryptophan synthetase.信函：色氨酸酶和色氨酸合成酶催化反应的立体化学与机制
J Am Chem Soc. 1976 Feb 18;98(4):1043-4. doi: 10.1021/ja00420a043.
5
Studies of enzyme-mediated reactions. Part IV. Complementary syntheses of stereospecifically labelled (R)- and (S)-[alpha-3H1]benzyl alcohol derivatives by use of liver alcohol dehydrogenase.酶介导反应的研究。第四部分。利用肝脏乙醇脱氢酶对立体特异性标记的(R)-和(S)-[α-³H₁]苄醇衍生物进行互补合成。
J Chem Soc Perkin 1. 1975(12):1156-61.
6
Stereochemistry of the formation of cysteine by O-acetylserine sulfhydrase.O-乙酰丝氨酸巯基酶催化形成半胱氨酸的立体化学
J Biol Chem. 1976 Sep 25;251(18):5478-82.