IL83604A - Phosphinothricin resistance gene obtainable from streptomyces viridochromogenes and its use - Google Patents

Phosphinothricin resistance gene obtainable from streptomyces viridochromogenes and its use

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Publication number
IL83604A
IL83604A IL8360487A IL8360487A IL83604A IL 83604 A IL83604 A IL 83604A IL 8360487 A IL8360487 A IL 8360487A IL 8360487 A IL8360487 A IL 8360487A IL 83604 A IL83604 A IL 83604A
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Israel
Prior art keywords
ptc
gene
ptt
resistance
fragment
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IL8360487A
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IL83604A0 (en
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Hoechst Ag
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Priority claimed from DE19863628747 external-priority patent/DE3628747A1/en
Priority claimed from DE19863642829 external-priority patent/DE3642829A1/en
Priority claimed from DE19873700313 external-priority patent/DE3700313A1/en
Application filed by Hoechst Ag filed Critical Hoechst Ag
Publication of IL83604A0 publication Critical patent/IL83604A0/en
Priority to IL8514398A priority Critical patent/IL85143A/en
Publication of IL83604A publication Critical patent/IL83604A/en

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    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
    • C12P41/006—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by reactions involving C-N bonds, e.g. nitriles, amides, hydantoins, carbamates, lactames, transamination reactions, or keto group formation from racemic mixtures
    • C12P41/007—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by reactions involving C-N bonds, e.g. nitriles, amides, hydantoins, carbamates, lactames, transamination reactions, or keto group formation from racemic mixtures by reactions involving acyl derivatives of racemic amines
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N15/00—Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
    • C12N15/09—Recombinant DNA-technology
    • C12N15/63—Introduction of foreign genetic material using vectors; Vectors; Use of hosts therefor; Regulation of expression
    • C12N15/64—General methods for preparing the vector, for introducing it into the cell or for selecting the vector-containing host
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N15/00—Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
    • C12N15/09—Recombinant DNA-technology
    • C12N15/63—Introduction of foreign genetic material using vectors; Vectors; Use of hosts therefor; Regulation of expression
    • C12N15/79—Vectors or expression systems specially adapted for eukaryotic hosts
    • C12N15/82—Vectors or expression systems specially adapted for eukaryotic hosts for plant cells, e.g. plant artificial chromosomes (PACs)
    • C12N15/8201—Methods for introducing genetic material into plant cells, e.g. DNA, RNA, stable or transient incorporation, tissue culture methods adapted for transformation
    • C12N15/8209—Selection, visualisation of transformants, reporter constructs, e.g. antibiotic resistance markers
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N15/00—Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
    • C12N15/09—Recombinant DNA-technology
    • C12N15/63—Introduction of foreign genetic material using vectors; Vectors; Use of hosts therefor; Regulation of expression
    • C12N15/79—Vectors or expression systems specially adapted for eukaryotic hosts
    • C12N15/82—Vectors or expression systems specially adapted for eukaryotic hosts for plant cells, e.g. plant artificial chromosomes (PACs)
    • C12N15/8241—Phenotypically and genetically modified plants via recombinant DNA technology
    • C12N15/8261—Phenotypically and genetically modified plants via recombinant DNA technology with agronomic (input) traits, e.g. crop yield
    • C12N15/8271—Phenotypically and genetically modified plants via recombinant DNA technology with agronomic (input) traits, e.g. crop yield for stress resistance, e.g. heavy metal resistance
    • C12N15/8274—Phenotypically and genetically modified plants via recombinant DNA technology with agronomic (input) traits, e.g. crop yield for stress resistance, e.g. heavy metal resistance for herbicide resistance
    • C12N15/8277—Phosphinotricin
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/10—Transferases (2.)
    • C12N9/1025—Acyltransferases (2.3)
    • C12N9/1029—Acyltransferases (2.3) transferring groups other than amino-acyl groups (2.3.1)

Abstract

Selection of Streptomyces viridochromogenes DSM 4112 using phosphinothricyl-alanyl-alanine (PTT) results in PTT-resistant selectants. Subjecting the total DNA of these selectants to cutting with Bam HI, cloning of a 4.0 kb fragment and selection for PTT resistance result in the DNA fragment which harbours the phosphinothricin (PTC)-resistance gene. The latter is suitable for producing PTC-resistant plants, and as resistance marker and for the selective N-acetylation of the L form of racemic PTC. <IMAGE>

Description

83604/3 PHOSPHINOTHRICIN RESISTANCE GENE OBTAINABLE FROM STREPTOMYCES VIRIDOCHROMOGENES, AND ITS USE Eitan, Pearl, Latzer & Cohen-Zedek Advocates, Notaries and Patent Attorneys P-53996-IL HOECHST AKTIENGESELLSCHAFT HOE 86/F 206K Dr.KL/mL Specification Phosphinothricin-resistance gene, and its use Phosph i nothr i c i n (PTC, 2-am i no-4-me t hy I phosph i nobu t r i c acid) is an inhibitor of glutamine synthetase. PTC is a "structural unit" of the antibiotic phos ph i not h r i c y I -alanyl-alanine. This tripeptide (PTT) is active against Gram-positive and Gram-negative bacteria as well as against the fungus Bot r t i s c i ne rea (Bayer et al., Helv. Chim. Acta 55 (1972) 224). PTT is produced by the strain Streptomyces viridochromogenes Tu 494 (DSM 40736, DSM 4112).
German Patent 2,717,440 discloses that PTC acts as a total herbicide. The published PCT Application WO 86/ 02097 describes plants whose resistance to PTC is attributable to overproduction of glutamine synthetase. Overproduction of this type, for example resulting from gene amplification, entails the risks of instability. Hence, such an instability would be associated with a decrease in the overproduction of glutamine synthetase, and the competitive inhibitory action of PTC would reappear.
In contrast, the invention, which is defined in the patent claims, relates to a PTC - re s i s t ance gene and to its use for the production of PTC-r es i s tant plants. In addition, this gene can also be used as a resistance marker.
Furthermore, the gene is suitable for the selective N-acetylation of the L-form of racemic PTC.
The PTC-resistance gene according to the invention can be obtained by cutting, with BamHI, the total ONA from Streptomyces viridochromogenes OSM 4112 which has been selected for PTT resistance, by cloning a fragment 4.0 in size, and by selection for PTT resistance. The restriction map (figure 1) details the characteristics of this 4.0 kb fragment.
Cloning experiments on sections of this 4 kb fragment were carried out to localize the position of the coding region more accurately. It emerged from this that the resistance gene is located on the 1.6 kb Sstll-Sstl fragment (positions 0.55 to 2.15 in Fig. 1). Digestion with Bg 11 resulted in the fragment which is 0.8 kb in size and which, after incorporation into a plasmid and transformation of S_. i v i dans , confers PTT resistance. This resistance is caused by N-acetyl at ion of PCT.
Max am and Gilbert sequencing of the 0.8 kb fragment reveals DNA sequence I (Annex). The position of the resistance gene can be determined from the open reading frame of this sequence (from position 258). The end of the gene is located at the penultimate nucleotide shown (position 806), i.e. the last nucleotide (position 807) is the first of the stop codon.
The Sh ne-Dalgarno sequence in DNA sequence I is emphasized by underlining, as is the GTG acting as start codon. Thus, the top line depicts the definitive reading frame .
DNA sequence II shows the restriction sites within the sequenced gene. Enzymes which cut the sequence more than six times are not indicated.
The antibiotic PTT is taken up by bacteria and broken down to PTC. The latter also inhibits glutamine synthetase in bacteria, so that the bacteria die of a lack of glutamine. Hence, PTT-produc ing bacteria ought to have a mechanism which protects them from the action of PTT, that is to say either prevents reuptake of the PTT which has been produced or permits a modification of the breakdown product PTC. However, surprisingly, the PTT producer viridochromogenes DSM 4112 is sensitive to its own antibiotic. Unexpectedly, it proved possible however, by selection for PTT resistance to find, at the surprisingly high rate of 10~^, selectants which are resistant to PTT and, moreover, suppress the background growth of adjacent colonies.
A gene bank was set up from the DNA of these selectants by isolating the DNA and cleaving it with BamH I and ligating it into a St reptomycetes vector. The ligation mixture was transformed into the commercially available strain j>. I ividans TK 23, resulting in about 5000 to 10000 t r ansf ormants having an insert of about 1 to 5 kb per 1 \ig of ligation mixture. Among the transf ormants there were PTT-resistant S^. I i i dans strains. It was possible, by isolation of the plasmids and retransform-ation into I ividans, to show that the resistance is pi asmid-coded. The gene responsible for the resistance is located on a 4 kb BamH I fragment (Figure 1). The coding region is located on the 0.8 kb Bglll fragment.
The BamH I fragment contains no cleavage sites for the enzymes C a I , EcoR I , EcoRV, Hindlll, Hpa I , Kpn I , Pvul, PvuII and Xhol .
Comparison with the restriction map of a resistance gene, which has not been characterized in detail, for S. hygroscop i cus FERM BP-130/ATCC 21705 (European Patent Application with the publication no. 0,173,327, Figure 7) shows that the resistance gene according to the invention differs from the known gene, which was found during the search for PTT biosynthesis genes.
It was possible to show, by incubation of cell extracts frofn s. v i r i doc h r omogenes DSM 4112 and :S. i v i dans TK 23 on the one hand, and the PTT-resistant iridochromogenes selectants and a plasmid-carrying S. i i dans transform-ant, on the other hand, with PTC and acetyl-coenzyme A that the latter cells have acetylating activity.
- - Chromatography tests show that the acetylation takes place on the amino group.
Since PTT-res i s tance has also been found in E. co i , and thus the resistance mechanism also functions in Gram-negative bacteria, it is possible to rule out resistance based on transport phenomena. Thus, after coupling to plant promoters and using suitable vectors, the resistance gene according to the invention can be transformed into plants, and in this way PTC-res i stant plants can be produced.
The N-acetylat ion of PTC can also be used for race ate resolution of synthetic 0,L-PTC since selective acetylation of only the L-form takes place.
Thus the invention also relates to the use of the resistance gene for the selective N-acetylat ion of the L-form of racemic PTC.
The PTC acetyl transferase coded for by the resistance gene according to the invention can thus be used to separate racemic PTC, as can be obtained, for example, by the method of German Patent 2,717,440, into the optical antipodes by exposing the racemate to the acetylating action of this enzyme, since there is selective attack on the L-form while the D-form remains unchanged. The mixture thus obtained can then be fractionated in a manner known per se on the basis of the differences in propert ies.
The contacting of N-acyl-D,L-amino acids with acylases, which are immobilised on carriers where appropriate, with selective liberation of the L-amino acid, which can be extracted with water-immiscible solvents from the mixture with the N-acy l-D-amino acid after ac dif cation, has been disclosed (British Patent 1,369,462). A corresponding fractionation of N-ac I -0 , L-PTC is disclosed, - -for example, in German Of fenLegungsschr if t 2,939,269 or US Patent 4,226,941.
The D-PCT which remains according to the invention can be racemized in known manner (European Patent Application with the publication no. (EP-A) 0,137,371, example 8), and then returned to the process.
It is possible, but not necessary, to isolate the enzyme, this also being intended to mean, here and hereinafter, always the enzymat i cal ly active part. If the enzyme is isolated, it can be used in the free form or the form immobilised on a carrier. Examples of suitable carriers are described in EP-A 0,141,223. However, it is expedient not to isolate the enzyme but to use any desired PTC-resistant cells which express the enzyme according to the invention. Thus, it is possible and expedient to use the PTT-res i s tant selectants of S^. viridochromogenes DS 4112. Moreover, it is possible and advantageous to use any desired cell which has been transformed with the gene according to the invention and which is able to express PTC acetyltransferase. In this connection, the gene according to the invention, this also being intended to mean active parts thereof, can be introduced into the host cell in plasmid-integrated form or by using other customary methods of gene manipulation, for example by transf ect ion. For example, incorporation into a E. col i expression plasmid and transformation of E. col i with such a plasmid is expedient, for example by the methods known from EP-A 0,163,249 and 0,171,024.
For the N-acety I at ion, according to the invention, of L-PTC in the racemate the cells which express PTC acetyltransferase can be used in the free or immobilised form, with the customary methods of immobilisation being used (for example German Of fenlegungsschr if t 3,237,341 and literature cited therein).
The enzymatic acetylation, according to the invention, of L-PTC is carried out in the manner customary for enzymatic reactions, with the conditions of the method being governed by the characteristics of the organism used. In principle, methods suitable for th s are the same as for the abo emen t i oned selective deacylation method .
The invention is illustrated in detail in the examples which follow. Unless otherwise stated, parts and percentage data relate to weight.
Example 1: PTT-res i s t an t selectants The strain . v i r i doc h romogenes DSM 4112 was cultured on minimal medium (Hopwood et al., Genetic Manipulation of Streptomyces, A Laboratory Manual, The John Innes Foundation, Norwich, England (1985), page 233) and increasing concentrations of PTT were added. At a concentration of 100 ug/ml one resistant colony was found per 10^ colonies, approximately.
Example 2: Preparation of the vector The plasmid pSVHl (European Patent 0,070,522; US Patent 4,673,642) is cut with _Bg_lU, and the fragment about 7.1 kb in size is isolated and ligated with the 1.1 kb Bell fragment having thio-streptone resistance (European Patent Application with the publication number 0,158,201). The plasmid pEB2 which is about 8.15 kb in size is obtained (Figure 2).
Example 3: Isolation of the resistance gene The total DNA is isolated from the selectants obtained in example 1, and it is cleaved with BamHI . The plasmid pEB2 is likewise opened with BamH I , and the two mixtures are combined and ligated. The ligation mixture is transformed into S. lividans TK 23 (obtainable from the - - John Innes Foundation), with 5000 to 10000 transf ormants having an insert of about 1 - 5 kb being obtained per 1 \ig of Ligation mixture. Selection for PTT-res istance produces two resistant S^. i v i dans colonies- The plasmid which has been taken up is isolated from the latter and is cut with BamH I . A 4 kb BamH I fragment which carries the gene responsible for resistance is found. This plasmid was called pPRl (figure 3).
Ret ransf ormat i on into S^. I i v i dans TK 23 shows, that the PTT-resistance is plasmid-coded, since the t r ans f o r man ts grow on minimal medium containing 100 ug/ml PTT.
Example 4: Demonstration of the inactivation of PTC by N-acetyl at ion The following strains were examined to demonstrate the acetylating activity of the cloned fragment: v i r i -dochromogenes DSM 40736, j>. viridochromogenes (PTT-resistant mutant), S. v i dans T 23 and I i v i dans TK 23 (pPRD.
This entails the strains being inoculated into lysis medium A (European Patent Application with the publication number 0,158,872, page 6) and incubated at 30°C in an orbital shaker for 2 days. After harvesting, 1 mg of mycelium is disrupted with ultrasound in a suitable buffer (for example RS buffer: C. J. Thompson et al., J. Bacteriol. _1_L1 < 1982), 678-685). The procedure for a typical experiment to measure PTC breakdown is as follows: 100 μΐ of PTC solution (250 yg/ml ) and 50 μΐ of acetyl-CoA (4 mg/ml) are added to 250 μΐ of crude extract, and the mixture is incubated at 30°C for 2 hours. The amounts of PTC which are still present after this time are measured by HPLC. The results of this are as ol lows : Strain unreacted PTC introduced PTC S . I ividans TK23 100% S. v i r i doc h romogenes 72% (DSM 40736) > . vi r idochromogenes 7% Selectant S. lividans TK23 (pPRD 31% A comparison with reference substances on thin-Layer chromatography (no stain with ninhydrin) demonstrates that N-acety Lation of the PTC has taken pLace.
DNA Sequence I IleTrpSerA5p B1 ACTTCCGTAC6GABCC6CA6ACTCCBCAG6AGT6GATC6ACGACCT6SAGCBCCTCCAGG T6AAGGCAT6CCTC6GC6TCTGAGGC6TCCTCACCTA6CTGCT6GACCTCGCSGAGGTCC 3E7 RSAI , 3B0 HINFI. 394 BINI , 395 DPNI 5AU3A, 404 APYI ECOR II, 405 GSUI , 409 HAEII, 413 MNLI , 414 GSUI . 416 APYI ECORII , 419 AVAII, 21 ACCGCTACCCCTSGCTC6TCGCC6AG6T6BAB66C6TCBTCGCC66CATCGCCTACGCCG TG6C6ATG666ACC6AGCAGCG6CTCCACCTCCCGCA6CAGC6GCCGTA6CGGATGCGGC 430 APYI ECORII , 444 MNLI , 450 MNLI, 453 ACYI , 454 HGAI, 462 NAEI , 466 SFANI, 477 NAEI . 81 GCCCCT66AAGGCCCGCAAC6CCTAC6ACT66ACCGTCGA6TC6ACGGTGTACGTCTCCC CGGGGACCTTCC6GGCGTT6CGGAT6CT6ACCT6GCAGCTCAGCTGCCACAT6CA6AGGG 484 APYI ECORII, 511 AUAII. 519 HINFI, 521 ACCI HINCII SALI , 530 RSAI, 532 MAE 11 , DNA Sequence II (Continuation) 541 ACCGBCACCA6C66CTCGSACT5GGCTCCACCCTCTACACCCACCT6CTGAABTCCf TG6CCGTGGTC6CC6AGCCT6ACCC6A6GT6G6AGAT6TSGGT6GACGACTTCAGGTf 544 HBICI . 549 NSPBII , 5B3 HGIJII 5DUI . 572 MNLI . 578 TAQII , 583 BSPMI , 595 NCOI 5TYI , 596 NLAIII , B00 MNLI . 601 AG6CCCAGGSCTTCAAGAGCGTGGTCGCC6TCATCGGACTGCCCAACBACCCBABCSTGC TCCGGGTCCCGAAGTTCTCGCACCAGCGGCAGTAGCCTGACGGGTTGCTG6GCTCBCACS 805 APYI ECOR11. 650 AMI , £61 6CCTSCACGA6GCGCTCGBATACACCBCBCBCBBBACGCT6CSBSCABCC6SCTACAAGC CSSACSTGCTCCGCGAGCCTAT6TSBCBC6CBCCCTGCGACGCCCGTCGGCCGATSTTCG 669 MNLI , 671 HAEII , 686 FNUDII , 687 BSSHII , 688 FNUDII , 690 FNUDII , 695 HSAI , 69B BBVI , 705 BBUI , 70B NAEI . 716 TTH111I I . 721 ACGGGGBCTGSCACBACST6BBGTTCT6GCAGC6CGACTTCGAGCTGCCGGCCCCBCCCC T6CCCCCGACCBT6CTSCACCCCAABACCSTCSCBCT6AASCTCSACGGCC6GGGCGS5G 732 DRAIII , 736 MAEII , 749 BBUI . 753 FNUDII , 763 ALU] , 764 B BUI , 767 NAEI . 781 GCCCCGTCCGBCCCGTCACACAGATCT C6GGGCAGGCCGGGCAGTBTBTCTASA 795 MAEII I , 802 BSLII XHOII , 803 DPNI SAU3A ,

Claims (7)

83604/3 - 13 - We claim:
1. Phosphinothricin(PTC)-resistance gene obtainable by selecting Streptomyces viridochromogenes DSM 4112 for resistance to phosphinothricyl-alanyl-alanine (PTT), cutting with BamHI the total DNA from the resistant strains, cloning a fragment 4.0 kb in size, retransformation into sensitive S. lividans and selecting for PTT resistance.
2. The gene as claimed in Claim 1 , which has the restriction map shown in Figure 1.
3. The gene as claimed in Claim 1 , which has the DNA sequence I (Annex), positions 258-806.
4. A process for the production of PTC-resistant plants which comprises incorporating into the genome of the plant a gene as claimed in any one of claims 1 to 3.
5. A PTT-resistance marker in bacteria comprising the gene as claimed in any one of claims 1 to 3.
6. A PTC-resistance marker in plant cells comprising the gene as claimed in any one of claims 1 to 3.
7. A process for the selective N-acetylation of the L-form of racemic PTC which comprises contacting racemic PTC with a cell expressing the gene as claimed in any one of claims 1 to 3 or with the enzyme coded by these genes .
IL8360487A 1986-08-23 1987-08-21 Phosphinothricin resistance gene obtainable from streptomyces viridochromogenes and its use IL83604A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
IL8514398A IL85143A (en) 1987-01-21 1998-01-20 Resistance gene against phosphinothricin

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE19863628747 DE3628747A1 (en) 1986-08-23 1986-08-23 Phosphinothricin resistance gene and its use
DE3637307 1986-11-03
DE19863642829 DE3642829A1 (en) 1986-08-23 1986-12-16 Phosphinothricin-resistance gene
DE19873700313 DE3700313A1 (en) 1986-08-23 1987-01-08 Use of a phosphinothricin-resistance gene

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IL83604A0 IL83604A0 (en) 1988-01-31
IL83604A true IL83604A (en) 2004-02-19

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AT (1) ATE75776T1 (en)
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CN87105764A (en) 1988-11-30
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AU7731887A (en) 1988-05-19
HUT44621A (en) 1988-03-28
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JP2815847B2 (en) 1998-10-27
IL83604A0 (en) 1988-01-31
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EP0257542A3 (en) 1990-03-07
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