WO2011111073A2 - PROCÉDÉ DE BIOGENÈSE DE L-LYSINE À PARTIR DE ε-CAPROLACTAM OU DE PRODUITS INTERMÉDIAIRES ASSOCIÉS À LA DÉTÉRIORATION DE ε-CAPROLACTAM OU ISSUS DE LA DÉTÉRIORATION DE ε-CAPROLACTAM - Google Patents

PROCÉDÉ DE BIOGENÈSE DE L-LYSINE À PARTIR DE ε-CAPROLACTAM OU DE PRODUITS INTERMÉDIAIRES ASSOCIÉS À LA DÉTÉRIORATION DE ε-CAPROLACTAM OU ISSUS DE LA DÉTÉRIORATION DE ε-CAPROLACTAM Download PDF

Info

Publication number
WO2011111073A2
WO2011111073A2 PCT/IN2011/000162 IN2011000162W WO2011111073A2 WO 2011111073 A2 WO2011111073 A2 WO 2011111073A2 IN 2011000162 W IN2011000162 W IN 2011000162W WO 2011111073 A2 WO2011111073 A2 WO 2011111073A2
Authority
WO
WIPO (PCT)
Prior art keywords
caprolactam
lysine
adipic acid
degradation
amino
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/IN2011/000162
Other languages
English (en)
Other versions
WO2011111073A4 (fr
WO2011111073A3 (fr
Inventor
Anand Bhadalakar
Piyush Desai
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Individual
Original Assignee
Individual
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of WO2011111073A2 publication Critical patent/WO2011111073A2/fr
Publication of WO2011111073A3 publication Critical patent/WO2011111073A3/fr
Publication of WO2011111073A4 publication Critical patent/WO2011111073A4/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • C12P13/00—Preparation of nitrogen-containing organic compounds
    • C12P13/04—Alpha- or beta- amino acids
    • C12P13/08—Lysine; Diaminopimelic acid; Threonine; Valine

Definitions

  • the present invention relates to L-Lysine formation by biogenesis from ⁇ - caprolactam or ⁇ -caprolactam degradation or related intermediates selected from ⁇ - Amino Caproic Acid [ACA], Amino Adipic Acid, Adipic Acid, NorLe cine or any combinations thereof.
  • ACA ⁇ - Amino Caproic Acid
  • the present invention relates to biogenesis of L-Lysine by the microbial isolates belonging to groups selected from Groups Alcaligenes spp., Arthrobacter spp., Bacillus spp., Pseudomonas spp. & Rhodococcus spp. during degradation of ⁇ - caprolactam.
  • L-Lysine is an essential amino acid and is widely used as additive to human and animal food. It is also employed in medicine as component of infusion solutions.
  • Lysine is one of the eight amino acids identified as essential for animals and human beings. Thomas Burr Osborne and his associates at the Connecticut Agricultural Experiment Station found in the experiments with rats that a diet containing corn as the sole source protein (known to be deficient in lysine and tryptophan) produced obvious signs of malnutrition. Strikingly, in the children in the countries where corn is the principal food, there existed a high frequency of the protein-deficiency syndrome - Kwashiorkor [Harpstead, D. D. (1971) Sci Am. 225(2): 34-42].
  • Takashi et al in U.S. Pat. No. 3,770,585 describes a-amino-e-caprolactam (ACL) biotransformation process for production of L-Lysine by an enzymatic route.
  • ACL a-amino-e-caprolactam biotransformation process for production of L-Lysine by an enzymatic route.
  • the hydrolysing activity of microorganism belonging to Cryptococcus, Candida, Trichosporon and enzyme produced by said microorganisms brings about the conversion q a-amino-e-caprolactam (ACL) to L-Lysine via a selective hydrolytic step.
  • the present invention provides, biogenesis of L-Lysine from ⁇ - caprolactam or ⁇ -caprolactam degradation or related intermediates selected from the group of ⁇ - Amino Caproic Acid [AC A], Amino Adipic Acid, Adipic Acid, NorLeucine or any combinations thereof; by the biomass and more particularly selected from the groups like Alcaligenes spp., Arthrobacter spp., Bacillus spp. Pseudomonas spp. and Rhodococcus spp.
  • AC A ⁇ - Amino Caproic Acid
  • biogenesis of Lysine by degradation of ⁇ - caprolactam or ⁇ -caprolactam degradation or related intermediates selected from the group of ⁇ -Amiho Caproic Acid [ACA], Amino Adipic Acid, Adipic Acid, NorLeucine or any combinations thereof; comprises, contacting biomass and more particularly selected from the groups like Alcaligenes spp., Arthrobacter spp., Bacillus spp., Pseudomonas spp. and Rhodococcus spp.
  • ACA ⁇ -Amino Caproic Acid
  • biochemical reaction modulators particularly selected from the group like ammonium chloride, azide, o-phenanthroline, 8-hydroxyquinoline, pyridoxal phosphate, malonic acid and like.
  • the present invention provides a method of degradation ⁇ - caprolactam or ⁇ -caprolactam degradation intermediates selected from ⁇ -Amino Caproic Acid [ACA], Amino Adipic Acid, Adipic Acid, NorLeucine or combination thereof; to L-Lysine by processes which comprise the steps of:
  • NorLeucine or combination thereof in presence or absence of any one or combination of biochemical reaction modulators like ammonium chloride, azide, o-phenanthroline, 8-hydroxyquinoline, pyridoxal phosphate, malonic acid;
  • biochemical reaction modulators like ammonium chloride, azide, o-phenanthroline, 8-hydroxyquinoline, pyridoxal phosphate, malonic acid;
  • FIG. 1 Formation of Lysine
  • FIG. 2 Formation of Lysine by cultures R, B, F & Rh
  • FIG. 3 Cap degradation pathway describes the bacterial degradation of ⁇ - caprolactam.
  • the Lysine formation profile matched the log phase of the growth profile of the growth of cultures.
  • the essential amino acid is a product of primary metabolism.
  • Biotransformation medium consists of ⁇ -caprolactam or ⁇ -caprolactam degradation intermediates or any combinations thereof along with salts consisting of Mg +2 and PO4" 3 .
  • the Salts of Mg +2 are selected from group of Magnesium hydroxide, chloride, oxide, gluconate, malate, orotate, citrate, sulfate (inclusive of Epsom salts), borate or salicylate and Salts of P0 4 3 are selected from group of Potassium dihydro phosphate, Dipotassium hydrogen phosphate, Sodium phosphate, Magnesium phosphate, and likes and their mixtures thereof.
  • the medium employed for enrichment and cultivation of caprolactam utilizing micro-organisms contained caprolactam as sole carbon and nitrogen source with the following composition (g l 1 ): MgS0 4 .7H 2 0 0.70, KH2PO4 1.00, Caprolactam 10.00 (pH 7.6) [CM] .
  • the minimal medium without Caprolactam is also referred to as Basal Medium, elsewhere.
  • Ammonium chloride [0.6 g H] was supplemented depending upon the need. In the case of solid media, 2.5 g% of agar-agar was used.
  • caprolactam was replaced with ⁇ - caprolactam degradation intermediates selected from ⁇ -Amino Caproic Acid [ACA], Amino Adipic Acid, Adipic Acid, NorLeucine or combination thereof, other substrates like Sucrose ( l Og l 1 ), or ⁇ -Amino Caproic Acid [ACA] ( lOg H) for alternate media.
  • ACA ⁇ -Amino Caproic Acid
  • Amino Adipic Acid Adipic Acid
  • Adipic Acid NorLeucine or combination thereof
  • other substrates like Sucrose ( l Og l 1 )
  • ACA ⁇ -Amino Caproic Acid
  • Biomass was generated in rich medium like Luria Bertani medium, with 2% v/v inoculums, incubation on shaker at 180 rpm, and 30 ⁇ 2 °C.
  • the cells were thus, adapted to caprolactam for 7 hours on rotary shaker at 180 rpm.
  • the cells were then harvested by centrifugation in a bench-top medium-speed centrifuge at 10,000 x g for 10 minutes. Acetone treatment was given with chilled extrapure acetone twice for 15 minutes each at -20 °C.
  • biomass generated from defined medium the biomass generated from Caprolactam medium or Sucrose (+NH 4 C1) medium was harvested by centrifugation in a bench-top medium- speed centrifuge at 10,000 x g for 10 minutes and washed with one-tenth volume of normal saline. Acetone treatment was given with chilled extrapure acetone twice for 15 minutes each at -20 °C. Every time, the cells were thoroughly washed washed with extrapure acetone and centrifuged at 10,000 x g (Remi centrifuge) for 6 minutes. Such acetone-dried biomass was carefully collected weighed and small aliquots of the same stored at -20 °C till further use.
  • lysine was quantified by microbiological assay using the organism Pediococcus acidilactici (previously called as Leuconostoc mesenteroides) ATCC 8042 - a lysine auxotroph, following a method, essentially given by Meites (1963) [Difco Manual of dehydrated culture media and reagents; Difco Laboratories, Inc., Detroit, p. 233]. .
  • any of the substrates like ⁇ -caprolactam or ⁇ - caprolactam degradation intermediates selected from ⁇ -Amino Caproic Acid [ACA], Amino Adipic Acid, Adipic Acid, NorLeucine or combination thereof; in presence or absence of any one or combination of biochemical reaction modulators like ammonium chloride, azide, o-phenanthroline, 8- hydroxyquinoline, pyridoxal phosphate, malonic acid
  • biochemical reaction modulators like ammonium chloride, azide, o-phenanthroline, 8- hydroxyquinoline, pyridoxal phosphate, malonic acid
  • ACA ⁇ -Amino Caproic Acid
  • ⁇ -caprolactam or ⁇ -caprolactam degradation intermediates selected from ⁇ -Amino Caproic Acid [ACA], Amino Adipic Acid, Adipic Acid, NorLeucine or combination thereof gives pure L-Lysine by biogenesis.
  • microorganisms belonging to group Alcaligenes spp. belonged to Alcaligenes faecalis [designated as R or R, herein further]; microorganisms belonging to group Arthrobacter spp. belonged to Arthrobacter citreus [designated as F or fgc, herein further]; microorganisms belonging to group Bacillus spp. belonged to Bacillus sphaericus [designated B, herein further]; and microorganisms belonging to group Rhodococcus spp. belonged to Rhodococcus erythropolis [designated as Rh, herein further] [Fig. # 2].
  • ACA ⁇ -Amino Caproic Acid
  • biochemical reaction modulators like ammonium chloride, azide, o-phenanthroline, 8-hydroxyquinoline, pyridoxal phosphate, malonic acid;
  • CM Caprolactam Medium [in (g l 1 ): MgS0 4 .7H 2 0 0.70, KH 2 P0 4 1.00, Caprolactam 10.00 (pH 7.6)]
  • CM Caprolactam Medium
  • Microbial cultures viz. Alcaligenes faecalis [designated as R2 or R, herefurther], Arthrobacter citreus [designated as F or fgc herefurther], Bacillus sphaericus [designated as B, herefurther], and Rhodococcus erythropolis [designated as Rh, herefurther] grown in Luria-Bertani medium, washed in normal saline and resuspended in Caprolactam Medium [CM] [of Example I].
  • Alcaligenes faecalis designated as R2 or R, herefurther
  • Arthrobacter citreus designated as F or fgc herefurther
  • Bacillus sphaericus designated as B, herefurther
  • Rhodococcus erythropolis designated as Rh, herefurther
  • Example III the biomass is generated in the Luria-Bertani Medium, the biomass is washed with Normal Saline, adapted in Caprolactam Medium of Example I for 7 hours in shaking conditions at 180 rpm at 30 °C ⁇ 2 °C and then acetone treatment & rest of the processing and the reaction as in Example III.
  • the L-Lysine formed was in the range of 500 to 1500 ⁇ g/ 10 mg of acetone treated biomass/ml.
  • the biomass is generated in Defined Media viz. the Sucrose (+ Ammonium Chloride) Medium (Same as Caprolactam medium, with caprolactam being replaced by Sucrose 10 g H; NH 4 C1 0.6 g H), AND the Caprolactam medium [CM] and then acetone treatment & rest of the processing and the reaction as in Example III.
  • the L-Lysine formed was in the range of 500 to 1500 ⁇ g/ 10 mg of acetone treated biomass/ml.

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Microbiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Biotechnology (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Enzymes And Modification Thereof (AREA)

Abstract

La présente invention concerne un procédé de biogenèse de L-Lysine à partir de ε-caprolactam ou de produits intermédiaires associés à la détérioration de ε-caprolactam ou issus de la détérioration de ε-caprolactam sélectionnés parmi l'acide ε-amino caproïque [ACA], l'acide amino adipique, l'acide adipique, le Norleucine ou n'importe quelles combinaisons de ceux-ci, par des micro-organismes ou leurs enzymes, et plus particulièrement des micro-organismes appartenant aux groupes alcaligènes spp., Arthrobacter spp., Bacillus spp., Pseudomonas spp. et Rhodococcus spp.; dans un milieu de réaction. Le processus de biotransformation est réalisé et produit la biogenèse de L-Lysine à partir de ε-caprolactam ou de produits intermédiaires associés à la détérioration de ε-caprolactam ou issus de la détérioration de ε-caprolactam sélectionnés parmi l'acide ε-amino caproïque [ACA], l'acide amino adipique, l'acide adipique, le Norleucine ou n'importe quelles combinaisons de ceux-ci, en présence d'une combinaison de modulateurs/inhibiteurs; le procédé consiste ensuite à isoler la L-Lysine à partir du mélange de réaction.
PCT/IN2011/000162 2010-03-11 2011-03-10 PROCÉDÉ DE BIOGENÈSE DE L-LYSINE À PARTIR DE ε-CAPROLACTAM OU DE PRODUITS INTERMÉDIAIRES ASSOCIÉS À LA DÉTÉRIORATION DE ε-CAPROLACTAM OU ISSUS DE LA DÉTÉRIORATION DE ε-CAPROLACTAM Ceased WO2011111073A2 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
IN644/MUM/2010 2010-03-11
IN644MU2010 2010-03-11
IN668MU2011 2011-03-10
IN668/MUM/2011 2011-03-10

Publications (3)

Publication Number Publication Date
WO2011111073A2 true WO2011111073A2 (fr) 2011-09-15
WO2011111073A3 WO2011111073A3 (fr) 2011-11-03
WO2011111073A4 WO2011111073A4 (fr) 2012-01-05

Family

ID=44563944

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2011/000162 Ceased WO2011111073A2 (fr) 2010-03-11 2011-03-10 PROCÉDÉ DE BIOGENÈSE DE L-LYSINE À PARTIR DE ε-CAPROLACTAM OU DE PRODUITS INTERMÉDIAIRES ASSOCIÉS À LA DÉTÉRIORATION DE ε-CAPROLACTAM OU ISSUS DE LA DÉTÉRIORATION DE ε-CAPROLACTAM

Country Status (1)

Country Link
WO (1) WO2011111073A2 (fr)

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3056729A (en) * 1961-11-29 1962-10-02 Pfizer & Co C Process for preparing l-lysine by fermentation of the corresponding dllactam
US3770585A (en) * 1970-11-19 1973-11-06 Toray Industries Process for preparing l-lysine
US3796632A (en) * 1971-12-10 1974-03-12 Toray Industries Process for racemizing alpha-amino-epsilon-caprolactam
JPS6312292A (ja) * 1986-07-03 1988-01-19 Kyowa Hakko Kogyo Co Ltd Ｌ−リジンの製造法
JP2578463B2 (ja) * 1988-02-03 1997-02-05 協和醗酵工業株式会社 発酵法によるｌ−リジンの製造法
JP2817172B2 (ja) * 1989-03-07 1998-10-27 味の素株式会社 発酵法によるｌ―リジンの製法
KR20080113225A (ko) * 2006-03-09 2008-12-29 바스프 에스이 β-리신의 생산 방법

Also Published As

Publication number Publication date
WO2011111073A4 (fr) 2012-01-05
WO2011111073A3 (fr) 2011-11-03

Similar Documents

Publication Publication Date Title
Mukherjee et al. Studies on nutritional and oxygen requirements for production of L-asparaginase by Enterobacter aerogenes
JP4197754B2 (ja) 乳酸又はコハク酸の製造方法
FR2491495A1 (fr) Procede pour la production d'amino-acides par fermentation aerobie
Tsugawa et al. Production of l-Glutamic Acid from dl-Hydantoin-5-propionic Acid by Microoganisms: Part I. Screening of l-Glutamic Acid-Producing Microorganisms and Some Optimal Conditions for Production of l-Glutamic Acid
CA1219828A (fr) Cellules microbiennes productrices de phenylalanine ammonium lyase
JP3245881B2 (ja) 塩基性アミノ酸と酸性アミノ酸の同時発酵法
JP2950896B2 (ja) Ｄ―α―フェニルグリシンの製造法
KUBOTA et al. FERMENTATIVE PRODUCTION OF L-SERINE PRODUCTION OF L-SERINE FROM GLYCINE BY CORYNEBACTERIUM GLYCINOPHILUM NOV. SP.
US5188947A (en) Process and microorganism for producing l-ornithine by corynebacterium, brevibacterium, or athrobacter
US5196326A (en) Method for concurrent fermentation of basic amino acid and acidic amino acid
JP2952604B2 (ja) 発酵法によるアミノ酸の製造法
US6060267A (en) Production of vitamin B6 with an enzyme-containing cell extract
JPH01199589A (ja) 発酵法によるｌ−リジンの製造法
EP0455170B1 (fr) Procédé de culture de micro-organismes du genre Pseudomonas et procédé pour la préparation de L-alanine en utilisant ces micro-organismes
US5019503A (en) Method for production of l-threonine
EP0295622B1 (fr) Procédé pour la production de l-tryptophane
JP2618619B2 (ja) Ｄ−グルタミン酸の製造方法
JPH0362396B2 (fr)
US5036004A (en) Process for producing L-serine
JPS6312292A (ja) Ｌ−リジンの製造法
JP3090761B2 (ja) 光学活性乳酸の製造法
KR920005749B1 (ko) 신균주 코리네박테리움 글루타미쿰 mwex-46 및 이를 이용한 l-아르기닌의 제조방법
JPH0355116B2 (fr)
FR2658205A1 (fr) Procede pour la production simultanee d'un aminoacide basique et d'un aminoacide acide par fermentation.
EP0212972A2 (fr) Procédé de conversion biologique

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 11752951

Country of ref document: EP

Kind code of ref document: A2

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 11752951

Country of ref document: EP

Kind code of ref document: A2