两种与 cupin 超家族蛋白具有高度相似性的细菌羟腈裂解酶的特性。
Characterization of two bacterial hydroxynitrile lyases with high similarity to cupin superfamily proteins.
机构信息
Institute of Molecular Biotechnology, Graz University of Technology, Graz, Austria.
出版信息
Appl Environ Microbiol. 2012 Mar;78(6):2053-5. doi: 10.1128/AEM.06899-11. Epub 2012 Jan 6.
Abstract
Hydroxynitrile lyases (HNLs) catalyze the cleavage of cyanohydrins. In the reverse reaction, they catalyze the formation of carbon-carbon bonds by enantioselective condensation of hydrocyanic acid with carbonyls. In this study, we describe two proteins from endophytic bacteria that display activity in the cleavage and the synthesis reaction of (R)-mandelonitrile with up to 74% conversion of benzaldehyde (enantiopreference ee 89%). Both showed high similarity to proteins of the cupin superfamily which so far were not known to exhibit HNL activity.
摘要
羟腈裂解酶（HNLs）催化氰醇的裂解。在逆反应中，它们通过氰化氢与羰基的对映选择性缩合催化碳-碳键的形成。在这项研究中，我们描述了两种来自内生细菌的蛋白质，它们在（R）-扁桃腈的裂解和合成反应中表现出活性，苯甲醛的转化率高达 74%（对映体偏好 ee89%）。这两种蛋白质都与杯状蛋白超家族的蛋白质具有高度相似性，而这些蛋白质迄今尚未被发现具有 HNL 活性。
相似文献
1
Characterization of two bacterial hydroxynitrile lyases with high similarity to cupin superfamily proteins.两种与 cupin 超家族蛋白具有高度相似性的细菌羟腈裂解酶的特性。
Appl Environ Microbiol. 2012 Mar;78(6):2053-5. doi: 10.1128/AEM.06899-11. Epub 2012 Jan 6.
2
Discovery and molecular and biocatalytic properties of hydroxynitrile lyase from an invasive millipede, Chamberlinius hualienensis.来自入侵性千足虫花莲瘤马陆的醇腈酶的发现及其分子和生物催化特性
Proc Natl Acad Sci U S A. 2015 Aug 25;112(34):10605-10. doi: 10.1073/pnas.1508311112. Epub 2015 Aug 10.
3
Discovery of a novel (R)-selective bacterial hydroxynitrile lyase from Acidobacterium capsulatum.从荚膜红细菌中发现一种新型（R）-选择性细菌羟腈酶。
Comput Struct Biotechnol J. 2014 Jul 8;10(16):58-62. doi: 10.1016/j.csbj.2014.07.002. eCollection 2014 Jun.
4
Biochemical and structural characterization of a novel bacterial manganese-dependent hydroxynitrile lyase.新型细菌锰依赖羟腈酶的生化和结构特征。
FEBS J. 2013 Nov;280(22):5815-28. doi: 10.1111/febs.12501. Epub 2013 Sep 18.
5
Hydroxynitrile lyases from cyanogenic millipedes: molecular cloning, heterologous expression, and whole-cell biocatalysis for the production of (R)-mandelonitrile.来自产氰千足虫的羟腈裂解酶：（R）-扁桃腈生产的分子克隆、异源表达和全细胞生物催化。
Sci Rep. 2018 Feb 14;8(1):3051. doi: 10.1038/s41598-018-20190-x.
6
R-hydroxynitrile lyase from the cyanogenic millipede, Chamberlinius hualienensis-A new entry to the carrier protein family Lipocalines.台湾长尾马陆中的 R-羟腈裂解酶——载脂蛋白家族脂联素的新成员。
FEBS J. 2021 Mar;288(5):1679-1695. doi: 10.1111/febs.15490. Epub 2020 Aug 13.
7
Immobilized Baliospermum montanum hydroxynitrile lyase catalyzed synthesis of chiral cyanohydrins.固定化巴厘山桂花羟腈酶催化的手性氰醇合成。
Bioorg Chem. 2019 Mar;84:32-40. doi: 10.1016/j.bioorg.2018.11.017. Epub 2018 Nov 19.
8
Structure-Based Site-Directed Mutagenesis of Hydroxynitrile Lyase from Cyanogenic Millipede, Oxidus gracilis for Hydrocyanation and Henry Reactions.基于结构的氰醇裂解酶定点突变研究，来自产氰蜈蚣，秀丽氧丽金龟，用于氢氰化和 Henry 反应。
Chembiochem. 2024 Jun 3;25(11):e202400118. doi: 10.1002/cbic.202400118. Epub 2024 Apr 16.
9
Enantioselective Synthesis of Various Cyanohydrins Using Covalently Immobilized Preparations of Hydroxynitrile Lyase from Prunus dulcis.利用共价固定的甜杏仁腈水解酶制剂对多种氰醇进行对映选择性合成。
Appl Biochem Biotechnol. 2015 Nov;177(6):1348-63. doi: 10.1007/s12010-015-1819-4. Epub 2015 Aug 27.
10
Improvement of the amides forming capacity of the arylacetonitrilase from Pseudomonas fluorescens EBC191 by site-directed mutagenesis.通过定点诱变提高荧光假单胞菌EBC191中芳基乙腈酶的酰胺形成能力。
Appl Microbiol Biotechnol. 2015 Mar;99(6):2623-35. doi: 10.1007/s00253-014-6061-4. Epub 2014 Sep 24.
引用本文的文献
1
Structural characterization of Linum usitatissimum hydroxynitrile lyase: A new cyanohydrin decomposition mechanism involving a cyano-zinc complex.亚麻苦杏仁酶的结构特征：涉及氰基-锌配合物的新型氰醇分解机制。
J Biol Chem. 2022 Mar;298(3):101650. doi: 10.1016/j.jbc.2022.101650. Epub 2022 Jan 29.
2
β-Barrels and Amyloids: Structural Transitions, Biological Functions, and Pathogenesis.β-桶状结构和淀粉样纤维：结构转变、生物学功能与发病机制。
Int J Mol Sci. 2021 Oct 20;22(21):11316. doi: 10.3390/ijms222111316.
3
Synthesis of (R)-mandelic acid and (R)-mandelic acid amide by recombinant E. coli strains expressing a (R)-specific oxynitrilase and an arylacetonitrilase.重组大肠杆菌表达（R）-特异性羟腈酶和芳基乙腈酶合成（R）-扁桃酸和（R）-扁桃酸酰胺。
Biotechnol Lett. 2021 Jan;43(1):287-296. doi: 10.1007/s10529-020-02998-8. Epub 2020 Sep 16.
4
Effects of codon optimization and glycosylation on the high-level production of hydroxynitrile lyase from Chamberlinius hualienensis in Pichia pastoris.密码子优化和糖基化对台湾长尾萤光酶在巴斯德毕赤酵母中高效表达的影响。
J Ind Microbiol Biotechnol. 2019 Jul;46(7):887-898. doi: 10.1007/s10295-019-02162-w. Epub 2019 Mar 16.
5
Hydroxynitrile lyases from cyanogenic millipedes: molecular cloning, heterologous expression, and whole-cell biocatalysis for the production of (R)-mandelonitrile.来自产氰千足虫的羟腈裂解酶：（R）-扁桃腈生产的分子克隆、异源表达和全细胞生物催化。
Sci Rep. 2018 Feb 14;8(1):3051. doi: 10.1038/s41598-018-20190-x.
6
Enzyme discovery beyond homology: a unique hydroxynitrile lyase in the Bet v1 superfamily.超越同源性的酶发现：Bet v1 超家族中的一种独特的羟腈裂解酶。
Sci Rep. 2017 May 3;7:46738. doi: 10.1038/srep46738.
7
Discovery of a novel (R)-selective bacterial hydroxynitrile lyase from Acidobacterium capsulatum.从荚膜红细菌中发现一种新型（R）-选择性细菌羟腈酶。
Comput Struct Biotechnol J. 2014 Jul 8;10(16):58-62. doi: 10.1016/j.csbj.2014.07.002. eCollection 2014 Jun.
8
Hydroxynitrile lyases with α/β-hydrolase fold: two enzymes with almost identical 3D structures but opposite enantioselectivities and different reaction mechanisms.具有 α/β-水解酶折叠结构的羟腈裂解酶：两种具有几乎相同的 3D 结构但对映选择性相反且反应机制不同的酶。
Chembiochem. 2012 Sep 3;13(13):1932-9. doi: 10.1002/cbic.201200239. Epub 2012 Jul 31.
本文引用的文献
1
alpha-Hydroxynitrile lyase protein from Xylella fastidiosa: Cloning, expression, and characterization.来自桑氏假单胞菌的α-羟基腈裂合酶蛋白：克隆、表达及特性分析
Microb Pathog. 2009 Sep;47(3):118-27. doi: 10.1016/j.micpath.2009.06.007. Epub 2009 Jul 1.
2
Structure-based phylogeny as a diagnostic for functional characterization of proteins with a cupin fold.基于结构的系统发育分析作为一种用于具有cupin折叠的蛋白质功能表征的诊断方法。
PLoS One. 2009 May 29;4(5):e5736. doi: 10.1371/journal.pone.0005736.
3
Substrate binding in the FAD-dependent hydroxynitrile lyase from almond provides insight into the mechanism of cyanohydrin formation and explains the absence of dehydrogenation activity.杏仁中依赖黄素腺嘌呤二核苷酸的醇腈酶的底物结合为氰醇形成机制提供了见解，并解释了脱氢活性的缺失。
Biochemistry. 2009 Apr 21;48(15):3370-7. doi: 10.1021/bi802162s.
4
Cyanogenesis in plants and arthropods.植物和节肢动物中的氰化物生成
Phytochemistry. 2008 May;69(7):1457-68. doi: 10.1016/j.phytochem.2008.02.019. Epub 2008 Mar 18.
5
Bacterial endophytes: recent developments and applications.细菌内生菌：最新进展与应用
FEMS Microbiol Lett. 2008 Jan;278(1):1-9. doi: 10.1111/j.1574-6968.2007.00918.x. Epub 2007 Nov 21.
6
An efficient plasmid vector for expression cloning of large numbers of PCR fragments in Escherichia coli.一种用于在大肠杆菌中对大量PCR片段进行表达克隆的高效质粒载体。
Appl Microbiol Biotechnol. 2007 Nov;77(1):241-4. doi: 10.1007/s00253-007-1151-1. Epub 2007 Sep 5.
7
Potential and capabilities of hydroxynitrile lyases as biocatalysts in the chemical industry.醇腈酶作为化学工业中生物催化剂的潜力和能力。
Appl Microbiol Biotechnol. 2007 Aug;76(2):309-20. doi: 10.1007/s00253-007-1025-6. Epub 2007 Jul 3.
8
A novel screening assay for hydroxynitrile lyases suitable for high-throughput screening.一种适用于高通量筛选的新型羟基腈裂解酶筛选测定法。
J Biotechnol. 2007 Mar 30;129(1):151-61. doi: 10.1016/j.jbiotec.2006.10.004. Epub 2006 Oct 14.
9
Endophytic bacterial communities of field-grown potato plants and their plant-growth-promoting and antagonistic abilities.田间种植马铃薯植株的内生细菌群落及其促植物生长和拮抗能力。
Can J Microbiol. 2004 Apr;50(4):239-49. doi: 10.1139/w03-118.
10
Potential role of pathogen signaling in multitrophic plant-microbe interactions involved in disease protection.病原体信号在参与疾病保护的多营养级植物-微生物相互作用中的潜在作用。
Appl Environ Microbiol. 2004 Mar;70(3):1836-42. doi: 10.1128/AEM.70.3.1836-1842.2004.
Zotero 插件