一种酶促酯水解的新机制。来自洗涤剂降解微生物的仲烷基硫水解酶导致构型翻转和碳 - 氧键断裂。
A novel mechanism of enzymic ester hydrolysis. Inversion of configuration and carbon-oxygen bond cleavage by secondary alkylsulphohydrolases from detergent-degrading micro-organisms.
作者信息
Bartholomew B, Dodgson K S, Matcham G W, Shaw D J, White G F
出版信息
Biochem J. 1977 Sep 1;165(3):575-80. doi: 10.1042/bj1650575.
Abstract
The hydrolysis was studied of potassium (+)-octan-2-yl sulphate by two analogous, optically stereospecific, secondary alkylsulphohydrolases purified from two detergent-degrading micro-organisms, Comamonas terrigena and Pseudomonas C12B. Polarimetry studies have shown that (+)-octan-2-yl sulphate prepared from (+)-octan-2-ol is hydrolysed by both enzymes to yield (-)-octan-2-ol. This inversion of configuration implies that the enzymes are catalysing the scission of the C-O bond of the C-O-S linkage, a type of bond scission apparently not hitherto encountered among hydrolytic enzymes acting on ester bonds. Enzymic hydrolysis of potassium (+)-octan-2-yl sulphate in the presence of H218O and analysis of hydrolysis products for the presence of 18O has confirmed that C-O bond scission (and not O-S bond scission) occurs with both enzymes.
摘要
研究了从两种降解洗涤剂的微生物——土生丛毛单胞菌和假单胞菌C12B中纯化得到的两种类似的、具有光学立体特异性的仲烷基硫酸水解酶对(+)-辛-2-基硫酸钾的水解作用。旋光测定研究表明，由(+)-辛-2-醇制备的(+)-辛-2-基硫酸酯被这两种酶水解生成(-)-辛-2-醇。这种构型反转意味着这些酶催化了C-O-S键中C-O键的断裂，这种键的断裂显然是迄今为止作用于酯键的水解酶中尚未遇到过的一种类型。在H₂¹⁸O存在的情况下对(+)-辛-2-基硫酸钾进行酶促水解，并分析水解产物中¹⁸O的存在情况，证实这两种酶都发生了C-O键的断裂（而不是O-S键的断裂）。
相似文献
1
A novel mechanism of enzymic ester hydrolysis. Inversion of configuration and carbon-oxygen bond cleavage by secondary alkylsulphohydrolases from detergent-degrading micro-organisms.一种酶促酯水解的新机制。来自洗涤剂降解微生物的仲烷基硫水解酶导致构型翻转和碳 - 氧键断裂。
Biochem J. 1977 Sep 1;165(3):575-80. doi: 10.1042/bj1650575.
2
Purification and properties of the S1 secondary alkylsulphohydrolase of the detergent-degrading micro-organism, Pseudomonas C12B.降解洗涤剂的微生物假单胞菌C12B的S1仲烷基磺基水解酶的纯化及性质
Biochem J. 1978 Mar 1;169(3):659-67. doi: 10.1042/bj1690659.
3
Substrate specificity and other properties of the inducible S3 secondary alkylsulphohydrolase purified from the detergent-degrading bacterium Pseudomonas C12B.从降解洗涤剂的假单胞菌C12B中纯化得到的可诱导S3仲烷基硫水解酶的底物特异性及其他特性。
Biochem J. 1980 Apr 1;187(1):181-90. doi: 10.1042/bj1870181.
4
The mechanism of action of primary alkylsulphohydrolase and arylsulphohydrolase from a detergent-degrading micro-organism.一种降解洗涤剂的微生物中伯烷基硫酸酯酶和芳基硫酸酯酶的作用机制。
Biochem J. 1977 Dec 1;167(3):843-6. doi: 10.1042/bj1670843.
5
Preparation and characterization of substrates suitable for the study of stereospecific secondary alkylsulphohydrolases of detergent-degrading micro-organisms.适用于研究洗涤剂降解微生物立体特异性仲烷基硫酸水解酶的底物的制备与表征
Biochem J. 1977 Dec 1;167(3):717-22. doi: 10.1042/bj1670717.
6
Purification, properties and cellular localization of the stereospecific CS2 secondary alkylsulphohydrolase of Comamonas terrigena.土生丛毛单胞菌立体特异性二硫化碳仲烷基硫水解酶的纯化、性质及细胞定位
Biochem J. 1977 Dec 1;167(3):723-9. doi: 10.1042/bj1670723.
7
Purification and some properties of the D-lactate-2-sulphatase of Pseudomonas syringae GG.丁香假单胞菌GG的D-乳酸-2-硫酸酯酶的纯化及某些性质
Biochem J. 1984 Oct 15;223(2):487-94. doi: 10.1042/bj2230487.
8
Further studies on the substrate specificity and inhibition of the stereospecific CS2 secondary alkylsulphohydrolase of Comamonas terrigena.对土生丛毛单胞菌立体特异性二硫化碳仲烷基硫水解酶的底物特异性和抑制作用的进一步研究。
Biochem J. 1980 Nov 1;191(2):467-73. doi: 10.1042/bj1910467.
9
Chemically defined inducers of alkylsulphatases present in Pseudomonas C12B.假单胞菌C12B中存在的烷基硫酸酯酶的化学定义诱导剂。
Biochem J. 1974 Jan;138(1):53-62. doi: 10.1042/bj1380053.
10
Microbial alkyl- and aryl-sulfatases: mechanism, occurrence, screening and stereoselectivities.微生物烷基-和芳基-硫酸酯酶：机制、发生、筛选和立体选择性。
Appl Microbiol Biotechnol. 2014 Feb;98(4):1485-96. doi: 10.1007/s00253-013-5438-0. Epub 2013 Dec 19.
引用本文的文献
1
Enantiometric enrichment of R(-)-alkan-2-ols using a stereospecific alkylsulphatase.
Appl Microbiol Biotechnol. 1991 Jun;35(3):312-316. doi: 10.1007/BF00172718.
2
A stereoselective inverting sec-alkylsulfatase for the deracemization of sec-alcohols.一种对映选择性反转的仲烷基亚硫酸酯酶，用于仲醇的外消旋化。
Org Lett. 2011 Aug 19;13(16):4296-9. doi: 10.1021/ol201635y. Epub 2011 Jul 19.
3
Initiation of Activation of a Preemergent Herbicide by a Novel Alkylsulfatase of Pseudomonas putida FLA.新型恶臭假单胞菌 FLA 烷基磺酸盐酶对芽前除草剂的激活作用。
Appl Environ Microbiol. 1983 Nov;46(5):988-94. doi: 10.1128/aem.46.5.988-994.1983.
4
Purification and characterization of an inverting stereo- and enantioselective sec-alkylsulfatase from the gram-positive bacterium Rhodococcus ruber DSM 44541.从革兰氏阳性细菌红球菌DSM 44541中纯化和鉴定一种具有立体和对映体选择性的反式仲烷基硫酸酯酶
Appl Environ Microbiol. 2003 May;69(5):2810-5. doi: 10.1128/AEM.69.5.2810-2815.2003.
5
An improved procedure for the preparation of alkyl sulphate esters suitable for the study of secondary alkylsulphohydrolase enzymes.一种改进的制备适用于仲烷基硫酸酯酶研究的烷基硫酸酯的方法。
Biochem J. 1980 Apr 1;187(1):191-6. doi: 10.1042/bj1870191.
6
Substrate specificity and other properties of the inducible S3 secondary alkylsulphohydrolase purified from the detergent-degrading bacterium Pseudomonas C12B.从降解洗涤剂的假单胞菌C12B中纯化得到的可诱导S3仲烷基硫水解酶的底物特异性及其他特性。
Biochem J. 1980 Apr 1;187(1):181-90. doi: 10.1042/bj1870181.
7
Stimulation of bacterial arylsulfatase activity by arylamines: evidence for substrate activation.芳胺对细菌芳基硫酸酯酶活性的刺激作用：底物激活的证据。
J Bacteriol. 1981 Jul;147(1):69-74. doi: 10.1128/jb.147.1.69-74.1981.
8
The metabolism of lithocholic acid and lithocholic acid-3-alpha-sulfate by human fecal bacteria.人粪便细菌对石胆酸和石胆酸-3-α-硫酸盐的代谢
Lipids. 1982 Jul;17(7):477-82. doi: 10.1007/BF02535328.
9
Preliminary observations on alcohol dehydrogenases in Comamonas terrigena that exhibit stereospecificity towards secondary alcohols.对土生丛毛单胞菌中对仲醇表现出立体特异性的乙醇脱氢酶的初步观察。
Biochem J. 1980 Jun 1;187(3):703-9. doi: 10.1042/bj1870703.
10
Purification and properties of the P2 primary alkylsulphohydrolase of the detergent-degrading bacterium pseudomonas C12B.洗涤剂降解细菌假单胞菌C12B的P2伯烷基磺基水解酶的纯化及性质
Biochem J. 1980 Jan 1;185(1):23-31. doi: 10.1042/bj1850023.
本文引用的文献
1
Studies on sulphatases. 25. The determination of BaSO(3)O by infrared spectroscopy.硫酸酯酶研究。25. 用红外光谱法测定碱式硫酸钡。
Biochem J. 1959 Nov;73(3):442-7. doi: 10.1042/bj0730442.
2
Cleavage point during hydrolyses catalyzed by ribonuclease and phosphodiesterase.核糖核酸酶和磷酸二酯酶催化水解过程中的裂解点。
Biochim Biophys Acta. 1961 Oct 14;53:214-5. doi: 10.1016/0006-3002(61)90809-5.
3
Determination of inorganic sulphate in studies on the enzymic and non-enzymic hydrolysis of carbohydrate and other sulphate esters.碳水化合物及其他硫酸酯酶促水解和非酶促水解研究中无机硫酸盐的测定。
Biochem J. 1961 Feb;78(2):312-9. doi: 10.1042/bj0780312.
4
Studies on sulphatases. 20. Enzymic cleavage of aryl hydrogen sulphates in the presence of H218O.硫酸酯酶研究。20. 在H218O存在下芳基硫酸氢酯的酶促裂解。
Biochem J. 1958 May;69(1):155-9. doi: 10.1042/bj0690155.
5
Mechanism of action of 5'-nucleotidase.5'-核苷酸酶的作用机制。
J Biol Chem. 1956 Jul;221(1):469-76.
6
Solubilization of certain L- and D-Peptidases of hog kidney particulates.
Arch Biochem Biophys. 1952 Jul;39(1):230-1.
7
Studies on the enzymic degradation of L-serine O-sulphate by a rat liver preparation.大鼠肝脏制剂对L-丝氨酸O-硫酸酯的酶促降解研究。
Biochem J. 1967 Nov;105(2):467-72. doi: 10.1042/bj1050467.
8
The enzymic degradation of L-serine O-sulphate by a specific system from pig liver. Studies on the mechanism of the reaction.猪肝特定系统对L-丝氨酸O-硫酸盐的酶促降解。反应机制研究。
Biochem J. 1972 Jan;126(1):187-91. doi: 10.1042/bj1260187.
9
Chemically defined inducers of alkylsulphatases present in Pseudomonas C12B.假单胞菌C12B中存在的烷基硫酸酯酶的化学定义诱导剂。
Biochem J. 1974 Jan;138(1):53-62. doi: 10.1042/bj1380053.
10
Microbial sulfolipids. 3. The disulfate of (+)-1,14-docosanediol in Ochromonas danica.微生物硫脂。3. 丹麦赭球藻中（+）-1,14-二十二碳二醇的二硫酸盐
Biochemistry. 1969 Jul;8(7):2981-6. doi: 10.1021/bi00835a045.
Zotero 插件