JPH046355B2 - - Google Patents
Info
- Publication number
- JPH046355B2 JPH046355B2 JP25505587A JP25505587A JPH046355B2 JP H046355 B2 JPH046355 B2 JP H046355B2 JP 25505587 A JP25505587 A JP 25505587A JP 25505587 A JP25505587 A JP 25505587A JP H046355 B2 JPH046355 B2 JP H046355B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- gas
- produced
- negative
- aminoadipic
- 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.)
- Expired
Links
- OYIFNHCXNCRBQI-BYPYZUCNSA-N L-2-aminoadipic acid Chemical compound OC(=O)[C@@H](N)CCCC(O)=O OYIFNHCXNCRBQI-BYPYZUCNSA-N 0.000 claims description 23
- 244000005700 microbiome Species 0.000 claims description 14
- HXEACLLIILLPRG-UHFFFAOYSA-N pipecolic acid Chemical compound OC(=O)C1CCCCN1 HXEACLLIILLPRG-UHFFFAOYSA-N 0.000 claims description 13
- HXEACLLIILLPRG-RXMQYKEDSA-N l-pipecolic acid Natural products OC(=O)[C@H]1CCCCN1 HXEACLLIILLPRG-RXMQYKEDSA-N 0.000 claims description 10
- 241000589516 Pseudomonas Species 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 241000588986 Alcaligenes Species 0.000 claims description 6
- OYIFNHCXNCRBQI-UHFFFAOYSA-N 2-aminoadipic acid Chemical compound OC(=O)C(N)CCCC(O)=O OYIFNHCXNCRBQI-UHFFFAOYSA-N 0.000 claims description 2
- 238000012258 culturing Methods 0.000 claims 1
- 239000002253 acid Substances 0.000 description 51
- 239000007789 gas Substances 0.000 description 48
- 241000894006 Bacteria Species 0.000 description 13
- 239000000049 pigment Substances 0.000 description 12
- 229920001817 Agar Polymers 0.000 description 9
- 239000008272 agar Substances 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- WQZGKKKJIJFFOK-SVZMEOIVSA-N (+)-Galactose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-SVZMEOIVSA-N 0.000 description 6
- 108010010803 Gelatin Proteins 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
- 229920002472 Starch Polymers 0.000 description 6
- 230000002538 fungal effect Effects 0.000 description 6
- 239000008273 gelatin Substances 0.000 description 6
- 229920000159 gelatin Polymers 0.000 description 6
- 235000019322 gelatine Nutrition 0.000 description 6
- 235000011852 gelatine desserts Nutrition 0.000 description 6
- 239000008107 starch Substances 0.000 description 6
- 235000019698 starch Nutrition 0.000 description 6
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
- 230000001580 bacterial effect Effects 0.000 description 5
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- 239000002932 luster Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 3
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 3
- 102000016938 Catalase Human genes 0.000 description 3
- 108010053835 Catalase Proteins 0.000 description 3
- RFSUNEUAIZKAJO-VRPWFDPXSA-N D-Fructose Natural products OC[C@H]1OC(O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-VRPWFDPXSA-N 0.000 description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 3
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 3
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 3
- 238000003794 Gram staining Methods 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 3
- 229910002651 NO3 Inorganic materials 0.000 description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 3
- 102000004316 Oxidoreductases Human genes 0.000 description 3
- 108090000854 Oxidoreductases Proteins 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 description 3
- 108010046334 Urease Proteins 0.000 description 3
- MMDJDBSEMBIJBB-UHFFFAOYSA-N [O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[NH6+3] Chemical compound [O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[NH6+3] MMDJDBSEMBIJBB-UHFFFAOYSA-N 0.000 description 3
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000015271 coagulation Effects 0.000 description 3
- 238000005345 coagulation Methods 0.000 description 3
- 239000012228 culture supernatant Substances 0.000 description 3
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 238000009630 liquid culture Methods 0.000 description 3
- 235000013372 meat Nutrition 0.000 description 3
- 235000013336 milk Nutrition 0.000 description 3
- 239000008267 milk Substances 0.000 description 3
- 210000004080 milk Anatomy 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 230000001766 physiological effect Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000005720 sucrose Substances 0.000 description 3
- 235000000346 sugar Nutrition 0.000 description 3
- 238000000108 ultra-filtration Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000193830 Bacillus <bacterium> Species 0.000 description 2
- 241000282596 Hylobatidae Species 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- SRBFZHDQGSBBOR-HWQSCIPKSA-N L-arabinopyranose Chemical compound O[C@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-HWQSCIPKSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241000186809 Kurthia Species 0.000 description 1
- HXEACLLIILLPRG-YFKPBYRVSA-N L-pipecolic acid Chemical compound [O-]C(=O)[C@@H]1CCCC[NH2+]1 HXEACLLIILLPRG-YFKPBYRVSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000012136 culture method Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000012262 fermentative production Methods 0.000 description 1
- 210000003495 flagella Anatomy 0.000 description 1
- 235000013882 gravy Nutrition 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical class [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000013028 medium composition Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 239000000813 peptide hormone Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000003910 polypeptide antibiotic agent Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000019086 sulfide ion homeostasis Effects 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000011191 terminal modification Methods 0.000 description 1
- 229910021654 trace metal Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Description
〔産業上の利用分野〕
本発明は微生物を利用したＬ−α−アミノアジ
ピン酸を製造する方法に関する。
Ｌ−α−アミノアジピン酸は、非蛋白性のアミ
ノ酸である。このＬ−α−アミノアジピン酸は、
ペプチド性抗生物質やペプチドホルモンなどの生
理活性ペプチドの末端修飾剤として用いることが
できる。また、ペニシリンやセフアロスポリンに
代表されるβ−ラクラム系抗生物質の発酵生産に
おいて前駆体として利用できる。
〔従来の技術〕
しかしながら、Ｌ−α−アミノアジピン酸を簡
便に製造する方法は未だ確立されていない。トウ
モロコシ種子等中に少量存在するＬ−α−アミノ
アジピン酸を抽出する方法などが知られている
が、このような方法は、はん雑であり、かつ原料
の供給にも難点があるので、大量生産には適さな
い。
〔発明が解決しようとする問題点〕
本発明者は、このような従来法に代わるＬ−α
−アミノアジピン酸の製造について検討した結
果、純粋なＬ−ピペコリン酸、或は、DL−ピペ
コリン酸中に含まれるＬ−ピペコリン酸が、何種
類かの微生物によりＬ−α−アミノアジピン酸に
変換されることを見い出した。
〔問題を解決するための手段〕
本発明は、この知見に基き完成されたものであ
る。すなわち、本発明は、アルカリゲネス属、シ
ユウドモナス属及びクルシア属より選ばれ、Ｌ−
ピペコリン酸をＬ−α−アミノアジピン酸に変換
する能力を有する微生物をＬ−ピペコリン酸含有
培地で培養し、培養物からＬ−α−アミノアジピ
ン酸を採取することを特徴とする微生物によるＬ
−α−アミノアジピン酸の製造法を提供するもの
である。
Ｌ−ピペコリン酸をＬ−α−アミノアジピン酸
に変換する能力を有する微生物として、アルカリ
ゲネス属、シユウドモナス属、クルシア属より選
ばれ、代表菌として本発明者らが自然界より分離
したアルカリゲネス属No.309B1菌、シユードモナ
ス属No.520B菌、クルシア属No.113B菌を例示でき
る。
これらの微生物の菌学的性質は以下に示すとお
りである。
Γアルカリゲネス属No.309B1
形態
●直径約1μm、長さ約2μm程度の桿菌。（肉汁
寒天上で生育した菌体）
●グラム染色：陰性
●運動性であり、複数の周鞭毛を有する。
●芽胞形成能：なし。
次の各培地における生育状態
肉汁寒天平板培養
生育は、良好。コロニーの形状は、円形。菌
層の隆起は、偏平状。光沢は鈍光。色素生産
性、無し
肉汁寒天斜面培地
生育は、良好。生育形状は、拡布状。菌層の
隆起は、偏平状。光沢は鈍光。色素生産性、
無し。
肉汁液体培養
生育は認められるが、濁りは生ぜず、菌体は
沈澱する。色素生産性、無し。
肉汁ゼラチン穿刺培養
生育は不良。ゼラチン液化は、認められな
い。
リトマス・ミルク
培地をアルカリ性にする。凝固、液化は、認
められない。
次の生理学的性質
(1) 硝酸塩の還元：陰性
(2) 脱窒反応：陰性
(3) MRテスト：陰性
(4) VPテスト：陰性
(5) インドールの生成：陰性
(6) 硫化水素の生成：陰性
(7) デンプンの加水分解：陰性
(8) クエン酸の利用：Koserの培地および
Christensenの培地で陽性
(9) 無機窒素の利用
硝酸塩：陰性、アンモニウム塩：陽性
(10) 色素の生成：認められず。
(11) ウレアーゼ：陰性
(12) オキシダーゼ：陽性
(13) カタラーゼ：陽性
(14) 生育の範囲
温度：20〜40℃ PH：５〜８
(15) 酸素に対する態度：好気性
(16) Ｏ−Ｆテスト：グルコースより酸を生成
せず。
(17) 下記の糖類からの酸およびガスの生成
Ｌ−アラビノース：酸、ガスとも生成せ
ず。
Ｄ−キシロース：酸、ガスとも生成せ
ず。
Ｄ−グルコース：酸、ガスとも生成せ
ず。
Ｄ−マンノース：酸、ガスとも生成せ
ず。
Ｄ−フラクトース：酸、ガスとも生成せ
ず。
Ｄ−ガラクトース：酸、ガスとも生成せ
ず。
麦芽糖：酸、ガスとも生成せず。
シヨ糖：酸、ガスとも生成せず。
乳糖：酸、ガスとも生成せず。
トレハロース：酸、ガスとも生成せず。
Ｄ−ソルビツト：酸、ガスとも生成せ
ず。
Ｄ−マンニツト：酸、ガスとも生成せ
ず。
イノシツト：酸、ガスとも生成せず。
グリセリン：酸、ガスとも生成せず。
デンプン：酸、ガスとも生成せず。
以上の特徴はR.E.Buchanan、N.E.Gibbons編
バージエイズ マニユアル オブ デタミネイテ
イブ バクテリオロジイ８版「Bergey's
manual of Determinative Bacteriology 8th
Edition」及び長谷川武治編「微生物の同定と分
類、第１版」（学会出版センター、1981年）に記
載されているアルカリゲネス属（Alcaligenes属）
の特徴と一致している。本菌をアルカリゲネス属
No.309B1と命名し、FERM Ｐ−9314として寄託
されている。
Γシユウドモナス属No.520B菌
形態
●直径約1μm、長さ約2μm程度の桿菌。（肉汁
寒天上で生育した菌体）
●グラム染色：陰性
●運動性であり、一本の極鞭毛を有する。
●芽胞形成能：なし。
次の各培地における生育状態
肉汁寒天平板培養
生育は、良好。コロニーの形状は、円形。菌
層の隆起は、偏平状。光沢は鈍光。色素生産
性、無し
肉汁寒天斜面培地
生育は、良好。生育形状は、拡布状。菌層の
隆起は、偏平状。光沢は鈍光。色素生産性、
無し。
肉汁液体培養
生育は良好。均一に濁り、菌体の沈澱も認め
られる。色素生産性、無し。
肉汁ゼラチン穿刺培養
生育は良好。ゼラチン液化は、認められな
い。
リトマス・ミルク
培地を酸性にする。凝固が、認められる。
次の生理学的性質
(1) 硝酸塩の還元：陽性
(2) 脱窒反応：陽性
(3) MRテスト：陰性
(4) VPテスト：陰性
(5) インドールの生成：陰性
(6) 硫化水素の生成：陰性
(7) デンプンの加水分解：陽性
(8) クエン酸の利用：Koserの培地および
Christensenの培地で陽性
(9) 無機窒素の利用
硝酸塩：陽性、アンモニウム塩：陽性
(10) 色素の生成：認められず。
(11) ウレアーゼ：陽性
(12) オキシダーゼ：陽性
(13) カタラーゼ：陽性
(14) 生育の範囲
温度：10〜40℃ PH：５〜８
(15) 酸素に対する態度：好気性
(16) Ｏ−Ｆテスト：酸化的
(17) 下記の糖類からの酸およびガスの生成
Ｌ−アラビノース：酸を生成。ガスは、
生成せず。
Ｄ−キシロース：酸、ガスとも生成せ
ず。
Ｄ−グルコース：酸を生成。ガスは生成
せず。
Ｄ−マンノース：酸を生成。ガスは生成
せず。
Ｄ−フラクトース：酸を生成。ガスは生
成せず。
Ｄ−ガラクトース：酸を生成。ガスは生
成せず。
麦芽糖：酸、ガスとも生成せず。
シヨ糖：酸を生成。ガスは生成せず。
乳糖：酸を生成。ガスは生成せず。
トレハロース：酸を生成。ガスは生成せ
ず。
Ｄ−ソルビツト：酸を生成。ガスは生成
せず。
Ｄ−マンニツト：酸を生成。ガスは生成
せず。
イノシツト：酸を生成。ガスは生成せ
ず。
グリセリン：酸を生成。ガスは生成せ
ず。
デンプン：酸を生成。ガスは生成せず。
以上の特徴は前記のR.E.Buchanan、N.E.
Gibbons編バージエイズ マニユアル オブ デ
タミネイテイブ バクテリオロジイ８版
「Bergey's manual of Determinative
Bacteriology 8th Edition」及び長谷川武治編
「微生物の同定と分類、第１版」（学会出版センタ
ー、1981年）に記載されているシユードモナス属
（Pseudomonas属）の特徴と一致している。本菌
をシユードモナス属520B菌と命名し、FERM Ｐ
−No.9313として寄託されている。
Γクルシア属No.113B菌
形 態
●直径1μm、長さ2μm程度の桿菌（肉汁寒天上
で生育した菌体）
●グラム染色：陽性
●運動性であり、複数の周鞭毛を有する。
●芽胞形成能：なし
次の各培地における生育状態
肉汁寒天平板培養
生育は、良好。コロニーの形状は、円形。菌
層の隆起は、偏平状。光沢は鈍光。色素生産
性、無し。
肉汁寒天斜面培地
生育は、良好。生育形状は、拡布状。菌層の
隆起は、偏平状。色素生産性、無し。
肉汁液体培養
生育は認められるが、濁りは生ぜず、菌体は
沈澱する。色素生産性、無し。
肉汁ゼラチン穿刺培養
生育は不良。ゼラチン液化は、認められな
い。
リトマス・ミルク
培地をアルカリ性にする。凝固、液化は、認
められない。培地は粘稠になる。
次の生理学的性質
(1) 硝酸塩の還元：陰性
(2) 脱窒反応：陰性
(3) MRテスト：陰性
(4) VPテスト：陰性
(5) インドールの生成：陰性
(6) 硫化水素の生成：陰性
(7) デンプンの加水分解：陰性
(8) クエン酸の利用：Koserの培地および
Christensenの培地で陰性
(9) 無機窒素の利用
硝酸塩：陰性、アンモニウム塩：陰性
(10) 色素の生成：認められず。
(11) ウレアーゼ：陰性
(12) オキシダーゼ：陰性
(13) カタラーゼ：陽性
(14) 生育の範囲
温度：10〜40℃ PH：５〜８
(15) 酸素に対する態度：好気性
(16) Ｏ−Ｆテスト：グルコースから酸を生成
せず。
(17) 下記の糖類からの酸およびガスの生成
Ｌ−アラビノース：酸、ガスとも生成せ
ず。
Ｄ−キシロース：酸、ガスとも生成せ
ず。
Ｄ−グルコース：酸、ガスとも生成せ
ず。
Ｄ−マンノース：酸、ガスとも生成せ
ず。
Ｄ−フラクトース：酸、ガスとも生成せ
ず。
Ｄ−ガラクトース：酸、ガスとも生成せ
ず。
麦芽糖：酸、ガスとも生成せず。
シヨ糖：酸、ガスとも生成せず。
乳糖：酸、ガスとも生成せず。
トレハロース：酸、ガスとも生成せず。
Ｄ−ソルビツト：酸、ガスとも生成せ
ず。
Ｄ−マンニツト：酸ガスとも生成せず。
イノシツト：酸、ガスとも生成せず。
グリセリン：酸、ガスとも生成せず。
デンプン：酸、ガスとも生成せず。
以上の特徴は前記のR.E.Buchanan、N.E.
Gibbons編バージエイズ マニユアル オブ デ
タミネイテイブ バクテリオロジイ８版
「Bergey's manual of Determinative
Bacteriology 8th Edition」及び長谷川武治編
「微生物の同定と分類、第１版」（学会出版センタ
ー、1981年）に記載されているクルシア属
（Kurthia属）の特徴と一致する。本菌をクルシ
ア属No.113Bと命名し、FERM Ｐ−No.9312として
寄託されている。
本発明における具体的な培養は、Ｌ−ピペコリ
ン酸、或は、DL−ピペリコン酸の１〜20％水溶
液に（NH4）2SO4などの窒素源、K2HPO4や
KH2PO4などリン酸塩、各種微量金属塩を加え培
地としたもので前記の微生物を培養する。この際
の培地組成には、特に限定はない。また培養条件
にも制約はないが、PHは４−９、望ましくは
７、温度は、20℃〜50℃、望ましくは30℃、培養
方法は、振とう培養ないし通気培養が望ましい。
培養の経過と共に、培地中のＬ−ピペコリン酸
がＬ−α−アミノアジピン酸に変換され、培養液
中に蓄積される。すべてのＬ−ピペコリン酸がＬ
−α−アミノアジピン酸に変換されるのに要する
時間は、Ｌ−ピペコリン酸或はDL−ピペコリン
酸の初期濃度、用いる微生物及び培養条件によ
る。
蓄積されたＬ−α−アミノアジピン酸の培養液
からの回収は、通常の任意の方法を用いることが
できるが、等電点沈澱法が最も簡便である。すな
わち、培養液から遠心分離などにより菌体を除
き、培養液上清を得る。この培養液上清から蛋白
質等の高分子性物質を限外濾過により除く。次い
で、得られた濾液のPHを、Ｌ−α−アミノアジ
ピン酸の等電点である3.2に塩酸等で調整し、一
晩、低温下（４℃程度）に放置するとＬ−α−ア
ミノアジピン酸が沈殿する。この沈殿したＬ−α
−アミノアジピン酸を濾取し、冷水で洗浄した
後、乾燥すると、Ｌ−α−アミノアジピン酸の結
晶が得られる。
以上述べたように、本発明は、比較的安価でか
つ大量に入手できるDL−ピペコリン酸から簡便
にＬ−α−アミノアジピン酸を製造することを可
能にする。
次に、本発明を実施例により更に詳細に説明す
る。
〔実施例〕
DL−ピペコリン酸５％、KH2PO4、0.3％、
K2HPO40.3％、（NH4）2SO40.2％、MgSO4・
7H2O0.03％、NaCl0.01％、CaCl2・2H2O0.01％、
及び微量のマンガン、亜鉛、銅、鉄、モリブデ
ン、コバルトの塩を含むPH7.0の液体培地を滅菌
し、これにアルカリゲネス属No.309B1菌（FERM
Ｐ−9314）、シユードモナス属520B菌（FERM
Ｐ−9313）、クルシア属No.113B菌（FERM Ｐ−
9312）をそれぞれ接種し、３日間30℃で振とう培
養した。遠心分離により菌体を培養液から除去
し、培養液上清を得た。この培溶液上清を分画分
子量10000の限外濾過膜（アミコン社製、商品名
ダイアフローメンブレンPM10）を用いて限外濾
過を行ない高分子性物質を除いた。得られた濾液
のPHを５規定濃度の塩酸により3.2に調整し庫内
温度４℃の冷蔵庫内に１晩放置した。沈殿したＬ
−α−アミノアジピン酸を濾過により集め冷水で
数回洗浄した後、乾燥した。いずれの菌を用いた
場合でも、得られたＬ−α−アミノアジピン酸
は、アミノ酸分析システム（島津製作所製、商品
名LC−6Aアミノ酸分析システム）において１ピ
ークを与え、そのピークの保持時間は、標準品の
Ｌ−α−アミノアジピン酸の保持時間と一致して
いた。また、得られたＬ−α−アミノアジピン酸
の性状、融点、元素分析値、比施光度は標準品の
Ｌ−α−アミノアジピン酸と一致していた。それ
ぞれの菌を用いた場合の収率を次表に示す。
[Industrial Application Field] The present invention relates to a method for producing L-α-aminoadipic acid using microorganisms. L-α-aminoadipic acid is a non-protein amino acid. This L-α-aminoadipic acid is
It can be used as a terminal modification agent for physiologically active peptides such as peptide antibiotics and peptide hormones. It can also be used as a precursor in the fermentative production of β-laclam antibiotics, such as penicillin and cephalosporin. [Prior Art] However, a method for easily producing L-α-aminoadipic acid has not yet been established. Methods for extracting L-α-aminoadipic acid, which is present in small amounts in corn seeds, etc., are known, but such methods are complicated and have difficulties in supplying raw materials. Not suitable for mass production. [Problems to be solved by the invention] The present inventor has proposed an L-α alternative to such a conventional method.
- As a result of studying the production of aminoadipic acid, it was found that pure L-pipecolic acid or L-pipecolic acid contained in DL-pipecolic acid is converted to L-α-aminoadipic acid by several types of microorganisms. I found out that it can be done. [Means for solving the problem] The present invention has been completed based on this knowledge. That is, the present invention provides L-
L-α-aminoadipic acid produced by a microorganism is characterized in that a microorganism having the ability to convert pipecolic acid to L-α-aminoadipic acid is cultured in a medium containing L-pipecolic acid, and L-α-aminoadipic acid is collected from the culture.
A method for producing -α-aminoadipic acid is provided. Microorganisms that have the ability to convert L-pipecolic acid to L-α-aminoadipic acid are selected from the genera Alcaligenes, Pseudomonas, and Crucia, and the representative microorganism is Alcaligenes No. 309B1, which the present inventors isolated from nature. Bacteria, Pseudomonas genus No. 520B, and Crucia genus No. 113B can be exemplified. The mycological properties of these microorganisms are as shown below. Genus ΓAlcaligenes No.309B1 Morphology ●A bacillus with a diameter of approximately 1 μm and a length of approximately 2 μm. (Bacteria grown on broth agar) ● Gram staining: negative ● It is motile and has multiple periflagella. ●Spore forming ability: None. Growth status on each of the following media: Growth on broth agar plates is good. The shape of the colony is circular. The ridges of the fungal layer are flat. The luster is dull. Pigment productivity: None Growth on broth agar slant medium is good. The growth shape is spread-like. The ridges of the fungal layer are flat. The luster is dull. pigment productivity,
none. Growth in broth liquid culture is observed, but turbidity does not occur and the bacterial cells precipitate. Pigment productivity, none. Growth of meat juice gelatin puncture culture was poor. No gelatin liquefaction is observed. Make the litmus milk medium alkaline. No coagulation or liquefaction was observed. The following physiological properties (1) Nitrate reduction: negative (2) Denitrification reaction: negative (3) MR test: negative (4) VP test: negative (5) Indole formation: negative (6) Hydrogen sulfide formation : Negative (7) Starch hydrolysis: Negative (8) Utilization of citric acid: Koser's medium and
Positive with Christensen's medium (9) Utilization of inorganic nitrogen Nitrate: negative, ammonium salt: positive (10) Pigment formation: not observed. (11) Urease: Negative (12) Oxidase: Positive (13) Catalase: Positive (14) Growth range Temperature: 20-40℃ PH: 5-8 (15) Attitude towards oxygen: Aerobic (16) O-F Test: No acid production than glucose. (17) Generation of acid and gas from the following sugars L-arabinose: Neither acid nor gas is generated. D-xylose: Neither acid nor gas is produced. D-glucose: Neither acid nor gas is produced. D-mannose: Neither acid nor gas is produced. D-fructose: Neither acid nor gas is produced. D-galactose: Neither acid nor gas is produced. Maltose: Does not produce acid or gas. Sucrose: Does not produce acid or gas. Lactose: Does not produce acid or gas. Trehalose: Neither acid nor gas is produced. D-Sorbit: Neither acid nor gas is produced. D-mannite: Neither acid nor gas was produced. Inosit: Neither acid nor gas is produced. Glycerin: Does not produce acid or gas. Starch: Does not produce acid or gas. The above features can be found in Bergey's Manual of Determinative Bacteriology, 8th edition, edited by RE Buchanan and NE Gibbons.
manual of Determinative Bacteriology 8th
The genus Alcaligenes described in "Identification and Classification of Microorganisms, 1st Edition" edited by Takeharu Hasegawa (Gakkai Publishing Center, 1981)
is consistent with the characteristics of This bacterium belongs to the genus Alcaligenes.
It was named No. 309B1 and deposited as FERM P-9314. Γ Pseudomonas No.520B Bacteria Morphology ● Rod bacterium with a diameter of approximately 1 μm and a length of approximately 2 μm. (Bacteria grown on broth agar) ● Gram staining: Negative ● It is motile and has one polar flagellum. ●Spore forming ability: None. Growth status on each of the following media: Growth on broth agar plates is good. The shape of the colony is circular. The ridges of the fungal layer are flat. The luster is dull. Pigment productivity: None Growth on broth agar slant medium is good. The growth shape is spread-like. The ridges of the fungal layer are flat. The luster is dull. pigment productivity,
none. Growth in broth liquid culture is good. It becomes uniformly cloudy, and precipitated bacterial cells are also observed. Pigment productivity, none. Meat juice gelatin puncture culture growth is good. No gelatin liquefaction is observed. Acidify the litmus milk medium. Coagulation is observed. The following physiological properties (1) Nitrate reduction: Positive (2) Denitrification reaction: Positive (3) MR test: Negative (4) VP test: Negative (5) Indole production: Negative (6) Hydrogen sulfide production : Negative (7) Starch hydrolysis: Positive (8) Utilization of citric acid: Koser's medium and
Positive in Christensen's medium (9) Utilization of inorganic nitrogen Nitrate: positive, ammonium salt: positive (10) Pigment formation: not observed. (11) Urease: Positive (12) Oxidase: Positive (13) Catalase: Positive (14) Growth range Temperature: 10-40℃ PH: 5-8 (15) Attitude towards oxygen: Aerobic (16) O-F Test: Oxidative (17) Formation of acids and gases from the following sugars L-arabinose: Forms acids. The gas is
Not generated. D-xylose: Neither acid nor gas is produced. D-glucose: produces acid. No gas is produced. D-mannose: produces acid. No gas is produced. D-fructose: produces acid. No gas is produced. D-galactose: produces acid. No gas is produced. Maltose: Does not produce acid or gas. Sucrose: Produces acid. No gas is produced. Lactose: produces acid. No gas is produced. Trehalose: Produces acid. No gas is produced. D-Sorbit: Generates acid. No gas is produced. D-mannite: produces acid. No gas is produced. Inosites: Produces acid. No gas is produced. Glycerin: Generates acid. No gas is produced. Starch: produces acid. No gas is produced. The above characteristics are based on the above-mentioned RE Buchanan, NE
Bergey's manual of Determinative Bacteriology 8th edition edited by Gibbons
The characteristics match the characteristics of the genus Pseudomonas described in "Bacteriology 8th Edition" and "Identification and Classification of Microorganisms, 1st Edition" edited by Takeharu Hasegawa (Gakkai Publishing Center, 1981). This bacterium was named Pseudomonas 520B and FERM P
-Deposited as No.9313. Gamma Crucia No. 113B Bacteria Morphology ●Bacillus with a diameter of about 1 μm and length of about 2 μm (bacteria grown on broth agar) ●Gram staining: positive●Motile and has multiple periflagella. ●Spore-forming ability: None Growth status in each of the following media: Growth in broth agar plate culture is good. The shape of the colony is circular. The ridges of the fungal layer are flat. The luster is dull. Pigment productivity, none. Growth on gravy agar slant medium is good. The growth shape is spread-like. The ridges of the fungal layer are flat. Pigment productivity, none. Growth in broth liquid culture is observed, but turbidity does not occur and the bacterial cells precipitate. Pigment productivity, none. Growth of meat juice gelatin puncture culture was poor. No gelatin liquefaction is observed. Make the litmus milk medium alkaline. No coagulation or liquefaction was observed. The medium will become viscous. The following physiological properties (1) Nitrate reduction: negative (2) Denitrification reaction: negative (3) MR test: negative (4) VP test: negative (5) Indole formation: negative (6) Hydrogen sulfide formation : Negative (7) Starch hydrolysis: Negative (8) Utilization of citric acid: Koser's medium and
Negative in Christensen's medium (9) Utilization of inorganic nitrogen Nitrate: negative, ammonium salt: negative (10) Pigment formation: Not observed. (11) Urease: negative (12) Oxidase: negative (13) Catalase: positive (14) Growth range Temperature: 10-40℃ PH: 5-8 (15) Attitude towards oxygen: Aerobic (16) O-F Test: No acid produced from glucose. (17) Generation of acid and gas from the following sugars L-arabinose: Neither acid nor gas is generated. D-xylose: Neither acid nor gas is produced. D-glucose: Neither acid nor gas is produced. D-mannose: Neither acid nor gas is produced. D-fructose: Neither acid nor gas is produced. D-galactose: Neither acid nor gas is produced. Maltose: Does not produce acid or gas. Sucrose: Does not produce acid or gas. Lactose: Does not produce acid or gas. Trehalose: Neither acid nor gas is produced. D-Sorbit: Neither acid nor gas is produced. D-mannite: Neither acid gas is generated. Inosit: Neither acid nor gas is produced. Glycerin: Does not produce acid or gas. Starch: Does not produce acid or gas. The above features are based on the above-mentioned RE Buchanan, NE
Bergey's manual of Determinative Bacteriology 8th edition edited by Gibbons
The characteristics match the characteristics of the genus Kurthia described in "Bacteriology 8th Edition" and "Identification and Classification of Microorganisms, 1st Edition" edited by Takeharu Hasegawa (Gakkai Publishing Center, 1981). This bacterium was named Crucia genus No. 113B and has been deposited as FERM P-No. 9312. A specific culture in the present invention involves adding a nitrogen source such as (NH 4 ) 2 SO 4 , K 2 HPO 4 or
The above microorganisms are cultured in a medium containing phosphates such as KH 2 PO 4 and various trace metal salts. There is no particular limitation on the medium composition at this time. Although there are no restrictions on the culture conditions, the pH is 4-9, preferably 7, the temperature is 20°C to 50°C, preferably 30°C, and the culture method is preferably shaking culture or aerated culture. As the culture progresses, L-pipecolic acid in the medium is converted to L-α-aminoadipic acid and accumulated in the culture solution. All L-pipecolic acid is L
The time required for conversion to -α-aminoadipic acid depends on the initial concentration of L-pipecolic acid or DL-pipecolic acid, the microorganism used, and the culture conditions. Any conventional method can be used to recover accumulated L-α-aminoadipic acid from the culture solution, but isoelectric precipitation is the simplest method. That is, bacterial cells are removed from the culture solution by centrifugation or the like to obtain a culture supernatant. Polymer substances such as proteins are removed from this culture supernatant by ultrafiltration. Next, the pH of the obtained filtrate was adjusted to 3.2, which is the isoelectric point of L-α-aminoadipic acid, with hydrochloric acid, etc., and when it was left overnight at a low temperature (about 4°C), L-α-aminoadipic acid was dissolved. Acid precipitates. This precipitated L-α
-Aminoadipic acid is collected by filtration, washed with cold water, and then dried to obtain crystals of L-α-aminoadipic acid. As described above, the present invention makes it possible to easily produce L-α-aminoadipic acid from DL-pipecolic acid, which is relatively inexpensive and available in large quantities. Next, the present invention will be explained in more detail with reference to Examples. [Example] DL-pipecolic acid 5%, KH 2 PO 4 , 0.3%,
K 2 HPO 4 0.3%, (NH 4 ) 2 SO 4 0.2%, MgSO 4 .
7H2O0.03 %, NaCl0.01%, CaCl2・2H2O0.01 %,
A PH7.0 liquid medium containing small amounts of salts of manganese, zinc, copper, iron, molybdenum, and cobalt is sterilized, and then Alcaligenes No. 309B1 bacteria (FERM
P-9314), Pseudomonas 520B (FERM
P-9313), Crucia genus No.113B (FERM P-
9312) and cultured with shaking at 30°C for 3 days. The bacterial cells were removed from the culture solution by centrifugation to obtain a culture supernatant. This medium solution supernatant was subjected to ultrafiltration using an ultrafiltration membrane with a molecular weight cutoff of 10,000 (manufactured by Amicon, trade name: Diaflow Membrane PM10) to remove polymeric substances. The pH of the obtained filtrate was adjusted to 3.2 with 5N hydrochloric acid and left overnight in a refrigerator at an internal temperature of 4°C. Precipitated L
-α-aminoadipic acid was collected by filtration, washed several times with cold water, and then dried. Regardless of which bacteria is used, the obtained L-α-aminoadipic acid gives one peak in an amino acid analysis system (manufactured by Shimadzu Corporation, trade name: LC-6A amino acid analysis system), and the retention time of that peak is The retention time was consistent with that of the standard L-α-aminoadipic acid. Further, the properties, melting point, elemental analysis values, and specific light absorption of the obtained L-α-aminoadipic acid were consistent with those of the standard L-α-aminoadipic acid. The yield when using each bacteria is shown in the table below.
【表】
ノアジピン酸の重量
＊ 収率＝[Table] Weight of noadipic acid * Yield =
Claims (1)
ルシア属より選ばれ、Ｌ−ピペコリン酸をＬ−α
−アミノアジピン酸に変換する能力を有する微生
物をＬ−ピペコリン酸含有培地で培養し培養物か
らＬ−α−アミノアジピン酸を採取することを特
徴とする微生物によるＬ−α−アミノアジピン酸
の製造法。1 Selected from the genus Alcaligenes, Pseudomonas and Crucia, L-pipecolic acid is converted into L-α
- Production of L-α-aminoadipic acid using a microorganism, characterized by culturing a microorganism capable of converting it into aminoadipic acid in a medium containing L-pipecolic acid, and collecting L-α-aminoadipic acid from the culture. Law.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25505587A JPH0198495A (en) | 1987-10-09 | 1987-10-09 | Production of l-alpha-aminoadipic acid using microorganism |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25505587A JPH0198495A (en) | 1987-10-09 | 1987-10-09 | Production of l-alpha-aminoadipic acid using microorganism |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0198495A JPH0198495A (en) | 1989-04-17 |
| JPH046355B2 true JPH046355B2 (en) | 1992-02-05 |
Family
ID=17273521
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP25505587A Granted JPH0198495A (en) | 1987-10-09 | 1987-10-09 | Production of l-alpha-aminoadipic acid using microorganism |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0198495A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0819761B1 (en) * | 1995-04-07 | 2004-10-13 | Mercian Corporation | Process for producing l-2-aminoadipic acid |
-
1987
- 1987-10-09 JP JP25505587A patent/JPH0198495A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0198495A (en) | 1989-04-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |