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Title Organization and Regulation of Genes Involved in Nitrile Metabolism in Rhodococcus Rhodochrous J1( Dissertation 全 Organization and Regulation of Genes Involved in Nitrile Title Metabolism in Rhodococcus rhodochrous J1( Dissertation_全 文 ) Author(s) Komeda, Hidenobu Citation 京都大学 Issue Date 1996-05-23 URL https://doi.org/10.11501/3112279 Right Type Thesis or Dissertation Textversion author Kyoto University Organization and Regulation of Genes Involved in Nitrile Metabolism in Rhodococcus rhodochrous 1 l Hidenobu Komeda 1996 CONTENTS I~ J RO DUCTIO'\ CII APTER I Anal)sis of H igh Molecular-:\-1as ... "-ilrile H)dratase (H-'-lHase) Gen e Cluster Scctton I Re~ulatol) genes for the exprc,ston ol catal~tically active 11-!\Hase SectiOn 2 lno;crtion 'cqucnce IS/ /64 in the H-'\Ha... e gene cluster 15 CHAPTER II Analysis of Low Molecular-Mass Mtrile H) dratase (L-NHase) Gene C lust er Secuon I CX·currenc~ of amidase<> in Rhodococc u.\ rhodochrow J I ..,,... _ Sc<.:lion 2 Amtdase coupled with L-N H a~e: Sequenctng and cxprc,ston of the gene and purification and charactcntAtion or the gene product 26 Section 1 Rcgulatol) genes required for the amtdc dependent induction of L-1\iHasc Section4 Cobalt tram.porter linked 10 L NH a:.e 60 CIIAPTER Ill Genetic Ana l)sis of Nitrilase Secuon I Sequencing and o'erexpression of the nitrilasc gene (mt\) and identification of an essential cysteine residue 73 SectiOn 2 Transcripllonal regulation of meA CON CLUSION 97 RFI< ERENCES 101 ACKNOWLF.I)G EME NTS 107 PUBLIC ATIONS 10~ 1!\TRODUCTIO" ABBRE\'IATIOt'l.~ bp Base pair(s) N1tnlc compounds containing a cyano function.al group such as cyanoglycosidcs. CCCP C·trb<myl C) anidc-m-chlomphen) I h) dmtonc cyanohp1ds. mdolc-J -acctonatnle and ~ - cyano-L-alaninc arc fom1cd by <1 "idt.• r~Ulgc of plant'> Ul D..tlton (I). '\atnle compound' arc al'o '' idely manufactured and cxtcn<;i\cl) u~ed b) the chcmic;tl DEAE Dieth) laminoethyi ­ induSII)': acetonitrile io; used as <1 solvent. adiponitnlc is a precursor of 11) lon-6.6 and DR Direu repeaLs DTNB 'iS DllhiobJs(2 nitro~nzoJc acid) acl)·lonitrile i' produced as a prccur~or uf acrylic fiber~ and pl~t1cs. l\1trilc hcrhacidcs such a' HJPES ,V-2-IIy droxyethylpipcranne-.\> '-2 ethancsulfonic acid dichlobenil <= 2.6-dichlorobcauonitrik: commercial name ca... oron). hromll\~nil <= 3.5- H '\Hase High molecular mas' nitnlc hydrata-.c dibromo-4-hydrox) bcntonitrile: commercaal name Srorninil). iox) nil <= 3.5-diiodo-4- HPLC High-perfonnancl liquad chromatography hydroxyhcnlonatrilc: comrnercml nume Semrol) and Suc.:tril (= -t-(uctam>\ loxy) 3.5 lAA Indole ~ - acetic acid IPTG Isopropyl ~-D-thmgala~o:topyranosidc <hbromobcntoaHtnlc) arc also widcl) uo;ed in agriculture for rice. wheat. harlc), c·om and tx:rry. IR Inverted repeats fhc~o;c mtrilc\ havL' been wtdcly ch'itributed in our envmmmcnt 1n fonm ol Industrial wa~te IS lnscrtwn -;equcncc v.atcr and reo.;iduul agncuhural chemicals. and if their releu'c as not controlled. finall) ''ill kb Kllohasc(., > threaten the environment. Therefore. nHrile b an urgent target from the 'tandp01nt of kDa Kllodalton Km Machachs conswm environmental punlkation and prcsenation. In the authors laboratOI)' ot Kyoto Uni\CI".II) l NHasc Low molecular mass-mtnle hydratase mu:robaal degradatiOn of haghly tox1c mtrile!> has been -;tudaed to find that thcar dcgradauon can \.1r \1olecular ma-.s proceed through t'' o l.'ntymallc patlmayo; (:!): nitrile hydraw'c ( '\Hase. f::C -t.:.u .84) catalytcs \H..tsc '\atnle hydratase the hydr.uion ol a nitrile to the corre ... ponding amide whach " then con"encd to the acid plul> ORF Open reading frame PAGE Pol yael) !amide gel electrophoresis ammonium by anmJa,e (3). \\hale natrila<;e catal)zcs the direct hydrol)sis of a nitrile to the PCR Polymerase chaan rcacuon corresponding acid plu' ammonaum (4). Interest m both nitnle ·converting cntymcs hao; PTH Phcny llh1ohydantoin incrcal>mgly focused on their vcr... atile functions: biOS) nthcsis of the plant hormone. indole-3- SDS Sodaum dodecyll>ulfatc acctac acid. from indolc-3-acetonitnle !5-9). and entymatic production ot useful compounds SF6847 ~.:'5 Di-tert-butyl-4-hydroxybenzilidenemalononitnle from niLnlc~ ( 10>. sse Standard sahnc catr.Hc Rhodowc( II\ tlwc/()( hrmts J I, wh1ch was found 111 the author\ laboratory. ha' both Tris Tris(hydroxymcthyl)aminomethan mtrilc degrading puthways, depending on the inducer (I 0). When this 'ltra1n as cultured in a TNB 5 ·n1io 2 nitrobentoate medium contaimng isovalcronitrile a'i an mducer, only nitrilase I'> induced (II). The -.train also produces higher (II "'Ha-;c) ( 12) and lower molecular mass (L-1\Hase) \illa"e' ( 10). Both ~Hases requarc cobalt 1ons and am1dcs for the1r anducuon. They arc compo-.cd of two subunits. a and ~ (0. ... ubunit d1ffers in saze from ~-subunat an each. and ex- and P -;ubunit'i of II Nllao.;e daHcr from those of L-'Hiase). H-:•mase and L '\!Hase <trc induced by urca and cyclohc.xanecarboxamadc. respcctavcly.:. Usmg JmmobiliLcd cells conwining II 'Ha-.e. the industrial production ol acl) lam ide from acrylonitrile was started 10 1991 (JO,CKX) tons / ~ earl. llus I'> the fiN case 111 wh1ch b1otcchnolog) was applied in the petrochemical induo.;try and abo ·I- the first successful example of the introdul:tion of an industrial bioconvc1 swn pro<.:css for the Chapter I describes the organitation of the H-NHase gene cluster from R 'hmlochrous manufacture of a commodit) chemical ( 10>. J 1. Two regulatory genes (nhhC and nhhD) required for the expression of H NHasc were Both H-and L-l\ Ha.sc genes (nhhBI\ and nh/8 \, respectively) have been .:Inned from identified by using a host vector system 1n Rhudoconus. The H -NIIa'e gene cluster was also R. rlzodoclzrous Jl and sequenced (13). ln each of the H-and L Nlln"e genes. an open charactent.cd to clarify us unusual induc.tion mechanism m R. rhodochrous J I. 1\ possible reading frame (ORF) for the !3-subunit (nhhB and nh/8) is located ju:.t up:-.tream of that tor the insertion sequence. named LSJ 164, was fortuitously found in the intervening spHce between a-subunit (nhh 1 and nh/A ). This arrangement of the coding sequences is rc \ erse of the order nhhCD and nhhBA and 11s primary structure was characterized. The dic;tribution of JSJ /64- found m the NHa.se genes of Rhodococnts sp. ~-774 ( 14) and Pseudommw.\ c hloromphis 823 like element in the genomcs of vanou~ RhodtJCoccus stratns and other nitrile-metabolizing ( 15). '\trains is also presented. R. rlwtlochrous J I has great catal}tic potential for the hydration of nitrile\ lO the Chapter II describes the organilation of Lhe L -NHase gene cluster from R rhodochrous corresponding amtdes ( 16). In thts process, contamination of acr}lic ac1d formed b) am1dase J I. The author indicated the evidence of the occurrence of amidases in this stnun. The author in the strain cnuses lhe deterioration in the quality of the manufactured acrylamide: acrylamide 1s also cloned and sequenced an amidase gene (amdA). which is cons1dered to be linked to the L­ expected not to be changed 1nto acrylic ac1d as much as possible by the amidase. Therefore. it NHase gene. The recombinant R. rhodochrous J I amidase protem in E. coli was also is tmportant from an applied standpoint to investigate a.mdases coupled wuh NHascs in this produced, purified and characterized. This chapter also describes the analy~es on the stram. mechanism of the L-NHase gene expres~ion. In addition to nh/81\ encoding L-!\Hase. two Nitrilac;es that utilize benzonitrile and related aromatic nitrites a~ substrates have been regulatory genes (nh/C and nh/D) were required for the rumde-dependcnt induction or nh/BA by purified from P.~eu.domonas (17.18) lvocarclia sp. NCIB 11215 (19) and NCIB 11216 (20). using the transformation system in Rhodococcus. nlziC has a se4uence similarity to nhhC. Fusarium so/ani (21). Arthrobacter sp. (22). R. rhodochrous Jl (23) and Escherichw coli which is involved in the H-NHase expression. and amiC, which 1s considered to be a <>ensor transformed with a Klebsiella ozaenae plasmid DNA (24). Nitrilases that act on aliphatic protein for inducer amides in the expression system of an aliphatic amidase in PsPudomonas nitrites and al)lacetonitriles are also punfied from Rhodococcus rhndmhrous K22 (25) and aeruginosa, suggesting the products of both regulatOry genes (NhlC and NhhC) are likely to Alcaligenes faecalts J\13 (26). respective!). and characterized. The nitrilaseo; from R. sensor proteins for inducer amides. nhlf. which ic; situated between nh/BA and amdA. is rhodochrous J l, R. rhodorhrous K22 and t\. faecalis JM3 are all strongly induced by the similar to the bacterial genes encoding nickel transporters previously reported. The product of addition of isovaleronitrile to the medium (23.25.26), making large amounts of en1 yme nh/F, NhlF transports cobalt ions into the Rhodococcus and Escherichia coli host cells. The available for application in industrial production of a wide range of useful acids from mtriles. transporter specific for cobalt ions was characterized using the transformation <>ystem in However, the mechanisms that regulate nJtrilase expression have never been understood in Rhodococcus. these strains. All nitrilases so far reported arc classified as sulfllydryl entymes since they are Chapter Ill describes the analyses of the structure and induction mechanhm of the inactivated by lhiol reagents. The R. rhodocltrou.\ J I nttrilase is also inactivated by thiol nitrilase from R. rhodoc hrous JI. mainly at gene level. The nitrilac;e gene (mtA) from R reagents (23). An active cysteme residue hao; not yet been identified 111 any nitrilases. rhodochrous J I was found to be c;imilar to the bromoxynil mtrilase gene from Kleb.nella The genus Rhodococcus, a member of the class Actinomyc:etes (27), has recently o:aenae.
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