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ES2183584T3 - Procedimiento para la preparacion de (s) -3-hidroxi-gamma-butirolactona opticamente pura. - Google Patents

Procedimiento para la preparacion de (s) -3-hidroxi-gamma-butirolactona opticamente pura.

Info

Publication number
ES2183584T3
ES2183584T3 ES99935127T ES99935127T ES2183584T3 ES 2183584 T3 ES2183584 T3 ES 2183584T3 ES 99935127 T ES99935127 T ES 99935127T ES 99935127 T ES99935127 T ES 99935127T ES 2183584 T3 ES2183584 T3 ES 2183584T3
Authority
ES
Spain
Prior art keywords
enzymatic reaction
alpha
gamma
hydroxy
formula
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 - Lifetime
Application number
ES99935127T
Other languages
English (en)
Inventor
Jongpil Chun
Yik-Haeng Cho
Youngmi Park
Kyoungrok Roh
Hosung Yu
Daeil Hwang
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.)
Lotte Fine Chemical Co Ltd
Original Assignee
Samsung Fine Chemicals Co Ltd
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 Samsung Fine Chemicals Co Ltd filed Critical Samsung Fine Chemicals Co Ltd
Application granted granted Critical
Publication of ES2183584T3 publication Critical patent/ES2183584T3/es
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/32—Oxygen atoms
    • C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
    • 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
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/02—Oxygen as only ring hetero atoms
    • C12P17/04—Oxygen as only ring hetero atoms containing a five-membered hetero ring, e.g. griseofulvin, vitamin C
    • 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
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/14—Preparation of compounds containing saccharide radicals produced by the action of a carbohydrase (EC 3.2.x), e.g. by alpha-amylase, e.g. by cellulase, hemicellulase
    • 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
    • C12P19/00—Preparation of compounds containing saccharide radicals
    • C12P19/22—Preparation of compounds containing saccharide radicals produced by the action of a beta-amylase, e.g. maltose
    • 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
    • C12P7/00—Preparation of oxygen-containing organic compounds
    • C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
    • C12P7/42—Hydroxy-carboxylic acids
    • H—ELECTRICITY
    • H04—ELECTRIC COMMUNICATION TECHNIQUE
    • H04M—TELEPHONIC COMMUNICATION
    • H04M1/00—Substation equipment, e.g. for use by subscribers
    • H04M1/02—Constructional features of telephone sets
    • H04M1/04—Supports for telephone transmitters or receivers
    • H—ELECTRICITY
    • H04—ELECTRIC COMMUNICATION TECHNIQUE
    • H04M—TELEPHONIC COMMUNICATION
    • H04M1/00—Substation equipment, e.g. for use by subscribers
    • H04M1/60—Substation equipment, e.g. for use by subscribers including speech amplifiers
    • H04M1/6033—Substation equipment, e.g. for use by subscribers including speech amplifiers for providing handsfree use or a loudspeaker mode in telephone sets
    • H04M1/6041—Portable telephones adapted for handsfree use
    • H04M1/6058—Portable telephones adapted for handsfree use involving the use of a headset accessory device connected to the portable telephone
    • H04M1/6066—Portable telephones adapted for handsfree use involving the use of a headset accessory device connected to the portable telephone including a wireless connection
    • H—ELECTRICITY
    • H04—ELECTRIC COMMUNICATION TECHNIQUE
    • H04M—TELEPHONIC COMMUNICATION
    • H04M19/00—Current supply arrangements for telephone systems
    • H04M19/02—Current supply arrangements for telephone systems providing ringing current or supervisory tones, e.g. dialling tone or busy tone
    • H04M19/04—Current supply arrangements for telephone systems providing ringing current or supervisory tones, e.g. dialling tone or busy tone the ringing-current being generated at the substations
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biotechnology (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Microbiology (AREA)
  • Signal Processing (AREA)
  • Computer Networks & Wireless Communication (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Furan Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)

Abstract

Un procedimiento para producir (S)-3-hidroxi-gamma- butirolactona ópticamente pura expresado por la fórmula 1 siguiente a partir de fuente polisacárida, que comprende las etapas siguientes: (a) reacción enzimática, utilizando enzimas específicas para la degradación secuencial, de amilopectina a oligosa- cárido con enlace alfa-(1,4) expresado por la fórmula 2; (b) oxidación del oligosacárido, con la adición de base y oxidante, y esterificación subsiguiente con alcohol en presencia de un catalizador de ácido para dar el éster de ácido (S)-3,4-dihidroxibutírico expresado por la fórmula 3; y (c) ciclización del éster preparado de ácido (S)-3,4- dihidroxibutírico en presencia de un catalizador de ácido sin procesos de separación y purificación adicionales para dar (S)-3-hidroxi-gamma-butirolactona expresado por la fórmula 1, en donde, R representa grupo de alquilo lineal o ramificado con 1~5 carbonos, en donde dicha reacción enzimática se lleva a cabo mediante reacción enzimática de alfa-amilasa seguido de reacción enzimática de pululanasa, y en donde la alfa-amilasa restante después de la reacción enzimática de alfa-amilasa se inactiva antes de llevarse a cabo la reacción enzimática de la pululanasa.
ES99935127T 1998-07-24 1999-07-23 Procedimiento para la preparacion de (s) -3-hidroxi-gamma-butirolactona opticamente pura. Expired - Lifetime ES2183584T3 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
KR19980029912 1998-07-24

Publications (1)

Publication Number Publication Date
ES2183584T3 true ES2183584T3 (es) 2003-03-16

Family

ID=19545119

Family Applications (4)

Application Number Title Priority Date Filing Date
ES99935128T Expired - Lifetime ES2183585T3 (es) 1998-07-24 1999-07-23 Procedimiento para la preparacion de derivados de (s) -3-4-dihidroxibutirico opticamente puros.
ES99935127T Expired - Lifetime ES2183584T3 (es) 1998-07-24 1999-07-23 Procedimiento para la preparacion de (s) -3-hidroxi-gamma-butirolactona opticamente pura.
ES99935131T Expired - Lifetime ES2183587T3 (es) 1998-07-24 1999-07-23 Procedimiento continuo para la preparacion de derivados de acido (s) -3-4-dihidroxibutirico opticamente puros..
ES99935130T Expired - Lifetime ES2183586T3 (es) 1998-07-24 1999-07-23 Procedimiento continuo para la preparacion de (s) -3- hidroxi- gamma- butirolactona opticamente pura.

Family Applications Before (1)

Application Number Title Priority Date Filing Date
ES99935128T Expired - Lifetime ES2183585T3 (es) 1998-07-24 1999-07-23 Procedimiento para la preparacion de derivados de (s) -3-4-dihidroxibutirico opticamente puros.

Family Applications After (2)

Application Number Title Priority Date Filing Date
ES99935131T Expired - Lifetime ES2183587T3 (es) 1998-07-24 1999-07-23 Procedimiento continuo para la preparacion de derivados de acido (s) -3-4-dihidroxibutirico opticamente puros..
ES99935130T Expired - Lifetime ES2183586T3 (es) 1998-07-24 1999-07-23 Procedimiento continuo para la preparacion de (s) -3- hidroxi- gamma- butirolactona opticamente pura.

Country Status (10)

Country Link
US (4) US6251642B1 (es)
EP (5) EP1100954B1 (es)
JP (5) JP3364482B2 (es)
KR (5) KR100310935B1 (es)
CN (5) CN1166781C (es)
AU (5) AU5067699A (es)
CA (5) CA2338527A1 (es)
DE (4) DE69903444T2 (es)
ES (4) ES2183585T3 (es)
WO (5) WO2000005400A1 (es)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1166781C (zh) * 1998-07-24 2004-09-15 三星精密化学株式会社 制备光学纯(S)-3-羟基-γ-丁内酯的连续方法
US6713290B2 (en) * 1998-07-24 2004-03-30 Samsung Fine Chemicals Co., Ltd. Process for preparing optically pure (S)-3-hydroxy-γ-butyrolactone
US6239311B1 (en) * 2000-04-24 2001-05-29 Board Of Trustees Operating Michigan State University Process for the preparation of 3,4-dihydroxybutanoic acid and salts and lactones derived therefrom
KR100645665B1 (ko) * 2000-07-27 2006-11-13 에스케이 주식회사 (ｓ)-베타-하이드록시-감마-부티로락톤의 연속 제조방법
FR2819123B1 (fr) * 2000-12-29 2003-04-11 St Microelectronics Sa Pompe de charge a faible bruit pour boucle a verrouillage de phase
JP4824874B2 (ja) * 2001-07-19 2011-11-30 高砂香料工業株式会社 光学活性γ−ブチロラクトンの製造方法
ATE394384T1 (de) * 2002-09-18 2008-05-15 Sk Holdings Co Ltd Kontinuierliches verfahren zur herstellung von optisch reinem (s)-beta hydroxy- gamma- butyrolacton
US6713639B1 (en) 2002-10-28 2004-03-30 Council Of Scientific And Industrial Research Process for preparing enantiomerically pure (S)-3-hydroxy-gamma-butyrolactone
JP4545487B2 (ja) * 2004-05-28 2010-09-15 イハラケミカル工業株式会社 アニリド化合物の製造方法
KR100590857B1 (ko) 2005-02-05 2006-06-19 엔자이텍 주식회사 양이온교환수지를 이용한 3-히드록시-감마-부티로락톤의 제조 방법
WO2007100227A1 (en) * 2006-03-02 2007-09-07 Lg Chem, Ltd. Method for preparing (s)-3-hydroxy-gamma-butyrolactone using hydrolase
JP2008162902A (ja) * 2006-12-27 2008-07-17 Central Glass Co Ltd ジフルオロ酢酸エステルの製造方法
US8734697B2 (en) 2008-12-22 2014-05-27 The University Of Queensland Patch production
CN105669423B (zh) * 2016-01-08 2018-06-29 江西科技师范大学 4-(4-(苯甲氧基)苯基)-2-羟基丁酸的两种对映异构体的新合成方法

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US3791865A (en) 1969-05-12 1974-02-12 Staley Mfg Co A E High maltose syrups
US3986890A (en) 1972-02-21 1976-10-19 Akademie Der Wissenschaften Der Ddr Method of producing starch hydrolysis products for use as food additives
US3922200A (en) * 1974-03-18 1975-11-25 Cpc International Inc Enzymatic hydrolysis of granular starch
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AT362526B (de) * 1977-09-13 1981-05-25 Boehringer Mannheim Gmbh Verfahren und reagens zur bestimmung von alpha- -amylase
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CN1166781C (zh) * 1998-07-24 2004-09-15 三星精密化学株式会社 制备光学纯(S)-3-羟基-γ-丁内酯的连续方法

Also Published As

Publication number Publication date
JP3364482B2 (ja) 2003-01-08
EP1100952B1 (en) 2002-10-09
ES2183585T3 (es) 2003-03-16
WO2000005400A1 (en) 2000-02-03
CN1316008A (zh) 2001-10-03
KR20000011940A (ko) 2000-02-25
KR100310935B1 (ko) 2001-10-18
AU5067899A (en) 2000-02-14
WO2000005398A1 (en) 2000-02-03
CN1316013A (zh) 2001-10-03
KR100324475B1 (ko) 2002-02-27
EP1100953A1 (en) 2001-05-23
AU5067699A (en) 2000-02-14
AU5068099A (en) 2000-02-14
KR20000011938A (ko) 2000-02-25
WO2000005402A1 (en) 2000-02-03
DE69903441D1 (de) 2002-11-14
JP2002521031A (ja) 2002-07-16
US6251642B1 (en) 2001-06-26
CA2338756A1 (en) 2000-02-03
CA2338755A1 (en) 2000-02-03
EP1100954A1 (en) 2001-05-23
EP1100951B1 (en) 2002-10-09
US6288272B1 (en) 2001-09-11
US6124122A (en) 2000-09-26
CN1166782C (zh) 2004-09-15
EP1100952A1 (en) 2001-05-23
DE69903442D1 (de) 2002-11-14
CN1316011A (zh) 2001-10-03
DE69903444T2 (de) 2003-07-10
DE69903443D1 (de) 2002-11-14
KR100308524B1 (ko) 2001-09-26
JP2002521395A (ja) 2002-07-16
CN1144878C (zh) 2004-04-07
KR20000011942A (ko) 2000-02-25
CA2338527A1 (en) 2000-02-03
KR100324476B1 (ko) 2002-02-27
JP2002521033A (ja) 2002-07-16
DE69903442T2 (de) 2003-06-18
JP2002521032A (ja) 2002-07-16
DE69903443T2 (de) 2003-06-18
WO2000005401A1 (en) 2000-02-03
CA2338752A1 (en) 2000-02-03
KR20000011941A (ko) 2000-02-25
CA2338757A1 (en) 2000-02-03
DE69903441T2 (de) 2003-08-14
ES2183586T3 (es) 2003-03-16
EP1100951A1 (en) 2001-05-23
KR20000011939A (ko) 2000-02-25
CN1316012A (zh) 2001-10-03
CN1160468C (zh) 2004-08-04
AU5067999A (en) 2000-02-14
JP3512741B2 (ja) 2004-03-31
EP1100954B1 (en) 2002-10-09
EP1100948A1 (en) 2001-05-23
ES2183587T3 (es) 2003-03-16
CN1316010A (zh) 2001-10-03
EP1100953B1 (en) 2002-10-09
AU5067799A (en) 2000-02-14
CN1166781C (zh) 2004-09-15
JP2002521394A (ja) 2002-07-16
JP3614367B2 (ja) 2005-01-26
JP3614366B2 (ja) 2005-01-26
WO2000005399A1 (en) 2000-02-03
US6221639B1 (en) 2001-04-24
DE69903444D1 (de) 2002-11-14

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