[go: up one dir, main page]

WO2009017154A1 - ペプチドの製造方法 - Google Patents

ペプチドの製造方法 Download PDF

Info

Publication number
WO2009017154A1
WO2009017154A1 PCT/JP2008/063659 JP2008063659W WO2009017154A1 WO 2009017154 A1 WO2009017154 A1 WO 2009017154A1 JP 2008063659 W JP2008063659 W JP 2008063659W WO 2009017154 A1 WO2009017154 A1 WO 2009017154A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
peptide
converting
reacting
amino acid
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/JP2008/063659
Other languages
English (en)
French (fr)
Inventor
Yasuhiro Kajihara
Izumi Sakamoto
Yuri Nambu
Kazuhiro Fukae
Hiroaki Asai
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.)
Otsuka Chemical Co Ltd
Yokohama National University NUC
Yokohama City University
Original Assignee
Otsuka Chemical Co Ltd
Yokohama National University NUC
Yokohama City University
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
Priority to AU2008283317A priority Critical patent/AU2008283317B2/en
Priority to JP2009525431A priority patent/JP5517620B2/ja
Priority to BRPI0813858-3A priority patent/BRPI0813858B1/pt
Priority to RU2010107283/04A priority patent/RU2478105C2/ru
Priority to US12/671,238 priority patent/US8809258B2/en
Priority to EP08791890.0A priority patent/EP2184290B1/en
Priority to CN200880101043.1A priority patent/CN101796064B/zh
Priority to KR1020107004198A priority patent/KR101534881B1/ko
Application filed by Otsuka Chemical Co Ltd, Yokohama National University NUC, Yokohama City University filed Critical Otsuka Chemical Co Ltd
Priority to CA2694542A priority patent/CA2694542C/en
Priority to DK08791890.0T priority patent/DK2184290T3/en
Publication of WO2009017154A1 publication Critical patent/WO2009017154A1/ja
Anticipated expiration legal-status Critical
Priority to US14/261,615 priority patent/US20140235822A1/en
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/107—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides
    • C07K1/1072—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides by covalent attachment of residues or functional groups
    • C07K1/1077—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides by covalent attachment of residues or functional groups by covalent attachment of residues other than amino acids or peptide residues, e.g. sugars, polyols, fatty acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/107—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides
    • C07K1/113—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides without change of the primary structure
    • C07K1/1133—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides without change of the primary structure by redox-reactions involving cystein/cystin side chains
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/04—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/46—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates
    • C07K14/47—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates from mammals
    • C07K14/4701—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans from vertebrates from mammals not used
    • C07K14/4727—Mucins, e.g. human intestinal mucin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/10—Tetrapeptides
    • C07K5/1002—Tetrapeptides with the first amino acid being neutral
    • C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
    • C07K5/1008—Tetrapeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atoms, i.e. Gly, Ala
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/04—Linear peptides containing only normal peptide links
    • C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/001—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof by chemical synthesis

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biochemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Analytical Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Toxicology (AREA)
  • Zoology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

　本発明は、-SH基を有するアミノ酸残基を含むペプチドにおいて、前記-SH基を-OH基に変換することを特徴とするペプチドの製造方法であって、以下の工程(a)～(c)： (a)ペプチド中の-SH基とメチル化剤とを反応させることにより、前記-SH基を-SMe基に変換する工程；(b)工程(a)で得られた-SMe基とシアン化剤とを反応させることにより、反応中間体を生成する工程；及び(c)工程(b)と比較して塩基性条件下、工程(b)で得られた反応中間体を、-OH基を有するアミノ酸残基を含むペプチドに変換する工程；を含む、前記製造方法を提供する。
PCT/JP2008/063659 2007-07-31 2008-07-30 ペプチドの製造方法 Ceased WO2009017154A1 (ja)

Priority Applications (11)

Application Number Priority Date Filing Date Title
CN200880101043.1A CN101796064B (zh) 2007-07-31 2008-07-30 肽的制备方法
BRPI0813858-3A BRPI0813858B1 (pt) 2007-07-31 2008-07-30 Métodos para a produção de um peptídeo e de um glicopeptídeo
RU2010107283/04A RU2478105C2 (ru) 2007-07-31 2008-07-30 Способ получения пептида
US12/671,238 US8809258B2 (en) 2007-07-31 2008-07-30 Method for producing peptide
EP08791890.0A EP2184290B1 (en) 2007-07-31 2008-07-30 Method for producing peptide
AU2008283317A AU2008283317B2 (en) 2007-07-31 2008-07-30 Method for producing peptide
DK08791890.0T DK2184290T3 (en) 2007-07-31 2008-07-30 PROCEDURE FOR PEPTID PREPARATION
KR1020107004198A KR101534881B1 (ko) 2007-07-31 2008-07-30 펩티드의 제조방법
CA2694542A CA2694542C (en) 2007-07-31 2008-07-30 Method for producing peptide
JP2009525431A JP5517620B2 (ja) 2007-07-31 2008-07-30 ペプチドの製造方法
US14/261,615 US20140235822A1 (en) 2007-07-31 2014-04-25 Method for producing peptide

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2007199372 2007-07-31
JP2007-199372 2007-07-31

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US12/671,238 A-371-Of-International US8809258B2 (en) 2007-07-31 2008-07-30 Method for producing peptide
US14/261,615 Division US20140235822A1 (en) 2007-07-31 2014-04-25 Method for producing peptide

Publications (1)

Publication Number Publication Date
WO2009017154A1 true WO2009017154A1 (ja) 2009-02-05

Family

ID=40304384

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2008/063659 Ceased WO2009017154A1 (ja) 2007-07-31 2008-07-30 ペプチドの製造方法

Country Status (13)

Country Link
US (2) US8809258B2 (ja)
EP (2) EP2184290B1 (ja)
JP (1) JP5517620B2 (ja)
KR (1) KR101534881B1 (ja)
CN (2) CN102850442B (ja)
AU (1) AU2008283317B2 (ja)
BR (1) BRPI0813858B1 (ja)
CA (1) CA2694542C (ja)
DK (2) DK2767545T3 (ja)
RU (1) RU2478105C2 (ja)
SG (1) SG183068A1 (ja)
TW (1) TWI405770B (ja)
WO (1) WO2009017154A1 (ja)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010092943A1 (ja) 2009-02-10 2010-08-19 大塚化学株式会社 IgG-Fcフラグメント及びその製造方法
JP2010538063A (ja) * 2007-09-04 2010-12-09 イプセン ファルマ ソシエテ パール アクシオン サンプリフィエ ポリペプチドおよび蛋白質の化学的合成のための方法および中間体
WO2010133382A3 (de) * 2009-05-20 2011-09-29 Henkel Ag & Co. Kgaa Kosmetische zusammensetzung und verformungsverfahren für keratinische fasern
WO2013047846A1 (ja) 2011-10-01 2013-04-04 株式会社糖鎖工学研究所 糖鎖付加ポリペプチドおよび当該ポリペプチドを含む医薬組成物
US10053499B2 (en) 2013-03-29 2018-08-21 Glytech, Inc. Polypeptide having sialylated sugar chains attached thereto

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2662080C (en) 2006-09-07 2012-07-17 F. Hoffmann-La Roche Ag A process for the manufacture of snac (salcaprozate sodium)
BRPI1016151B1 (pt) * 2009-06-26 2021-01-19 Glytech, Inc. processo para produção de um tioéster de peptídeo, processos para a produção de um polipeptídeo, processo para a produção de um segundo intermediário utilizado para o processo para a produção do tioéster de peptídeo e processo para a remoção de uma marca para a purificação adicionada a um lado terminal c de uma proteína recombinante
BR112013022941B8 (pt) * 2011-03-10 2021-02-23 Glytech Inc método para fabricação de glicopeptídeo tendo cadeia de açúcar sialil e método para a fabricação de um derivado de sialilglicoasparagina
US9850469B2 (en) * 2014-03-17 2017-12-26 The Trustees Of The University Of Pennsylvania Methods of stapling and unstapling peptides and proteins
US11161911B2 (en) 2017-10-23 2021-11-02 Go Therapeutics, Inc. Anti-glyco-MUC1 antibodies and their uses
CN107973838B (zh) * 2017-12-06 2021-02-26 广州恒宁生物科技有限公司 一种促进皮肤损伤修复的小分子多肽及其应用
WO2020006449A1 (en) * 2018-06-29 2020-01-02 Go Therapeutics, Inc. Anti-glyc0-muc1 antibodies and their uses
JP6564539B1 (ja) * 2018-09-14 2019-08-21 長瀬産業株式会社 スルホン酸化合物によるペプチド精製方法

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996034878A1 (en) 1995-05-04 1996-11-07 The Scripps Research Institute Synthesis of proteins by native chemical ligation
JPH1077294A (ja) * 1996-07-10 1998-03-24 Ajinomoto Co Inc 新規アスパルチルジペプチドアミド誘導体及び甘味剤
WO2003008431A1 (en) 2001-06-19 2003-01-30 Otsuka Chemical Co.,Ltd. Process for producing sugar chain asparagine derivative
WO2004005330A1 (ja) 2002-07-05 2004-01-15 Otsuka Chemical Co., Ltd. 糖鎖アスパラギンを有する糖ペプチドの製造法及び該糖ペプチド
WO2004058984A1 (ja) 2002-12-24 2004-07-15 Otsuka Chemical Co., Ltd. 糖鎖アスパラギン誘導体、糖鎖アスパラギンおよび糖鎖ならびにそれらの製造法
WO2004058824A1 (ja) 2002-12-26 2004-07-15 Otsuka Chemical Co., Ltd. ３分岐型糖鎖アスパラギン誘導体、該糖鎖アスパラギン、該糖鎖およびそれらの製造方法
WO2004070046A1 (ja) 2003-02-04 2004-08-19 Otsuka Chemical Co., Ltd. 糖鎖アスパラギン誘導体の製造方法
WO2005010053A1 (ja) 2003-07-28 2005-02-03 Otsuka Chemical Co., Ltd. アミノ化複合型糖鎖誘導体及びその製造方法
WO2007011055A1 (ja) 2005-07-19 2007-01-25 Otsuka Chemical Co., Ltd. 糖鎖誘導体の製造方法、構造解析方法、及び糖鎖誘導体

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2745351B2 (ja) * 1991-02-14 1998-04-28 富士写真フイルム株式会社 ペプチド誘導体及びその用途
US20040018054A1 (en) * 2002-07-26 2004-01-29 David Rueckert Shadowless floating dock
CH696355A5 (de) * 2002-11-14 2007-05-15 Clariant Speciality Fine Chemi Katalytisches Verfahren zur Herstellung von Carbonyl-Verbindungen.
JP2005046261A (ja) * 2003-07-31 2005-02-24 Mizuno Corp 捕球具

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996034878A1 (en) 1995-05-04 1996-11-07 The Scripps Research Institute Synthesis of proteins by native chemical ligation
JPH1077294A (ja) * 1996-07-10 1998-03-24 Ajinomoto Co Inc 新規アスパルチルジペプチドアミド誘導体及び甘味剤
WO2003008431A1 (en) 2001-06-19 2003-01-30 Otsuka Chemical Co.,Ltd. Process for producing sugar chain asparagine derivative
WO2004005330A1 (ja) 2002-07-05 2004-01-15 Otsuka Chemical Co., Ltd. 糖鎖アスパラギンを有する糖ペプチドの製造法及び該糖ペプチド
WO2004058984A1 (ja) 2002-12-24 2004-07-15 Otsuka Chemical Co., Ltd. 糖鎖アスパラギン誘導体、糖鎖アスパラギンおよび糖鎖ならびにそれらの製造法
WO2004058824A1 (ja) 2002-12-26 2004-07-15 Otsuka Chemical Co., Ltd. ３分岐型糖鎖アスパラギン誘導体、該糖鎖アスパラギン、該糖鎖およびそれらの製造方法
WO2004070046A1 (ja) 2003-02-04 2004-08-19 Otsuka Chemical Co., Ltd. 糖鎖アスパラギン誘導体の製造方法
WO2005010053A1 (ja) 2003-07-28 2005-02-03 Otsuka Chemical Co., Ltd. アミノ化複合型糖鎖誘導体及びその製造方法
WO2007011055A1 (ja) 2005-07-19 2007-01-25 Otsuka Chemical Co., Ltd. 糖鎖誘導体の製造方法、構造解析方法、及び糖鎖誘導体

Non-Patent Citations (15)

* Cited by examiner, † Cited by third party
Title
CANCER BIOLOGY & THERAPY, vol. 6, no. 4, April 2007 (2007-04-01), pages 481 - 486
CLARK P.I. ET AL.: "Chemical mutations of papain. The preparation of Ser25- and Gly 25-papain", J.S.C. CHEM. COMM., vol. 24, 1977, pages 923 - 924 *
CRICH D. ET AL.: "Native chemical ligation at phenylalanine", J. AM. CHEM. SOC., vol. 129, no. 33, 21 July 2007 (2007-07-21), pages 10064 - 10065, XP008131264 *
D. CRICH ET AL., J. AM. CHEM. SOC., vol. 129, 2007, pages 10064
FEBS LETTERS, vol. 50, no. 3, February 1975 (1975-02-01)
KAJIWARA Y.: "To Peptide no Seimitsu Kagaku Gosei", NATURAL SCIENCE, vol. 57, 22 January 2007 (2007-01-22), pages 75 - 85 *
LEPLAWY T. ET AL.: "alpha-Methylcysteine and its peptide chemistry", AMINO ACIDS, vol. 5, no. 3, 1993, pages 441, XP008129804 *
NARAYAN R.S. ET AL.: "Versatile and stereoselective syntheses of orthogonally protected beta-methylcysteine and beta-methyllanthionine", ORGANIC LETT., vol. 7, no. 13, 2005, pages 2655 - 2658, XP002393401 *
OKAMOTO R. ET AL.: "Tan'itsu Kozo no Tosa o Yusuru To Tanpakushitsu no Gosei Kenkyu", DAI 27 KAI THE JAPANESE SOCIETY OF CARBOHYDRATE RESEARCH NENKAI YOSHISHU, 10 July 2007 (2007-07-10), pages 63 *
PROTEIN SCIENCE, vol. 16, 2007, pages 2056 - 2064
SASAOKA S. ET AL.: "Tosaka Ovomucoid no Gosei Kenkyu", CSJ: THE CHEMICAL SOCIETY OF JAPAN DAI 87 SHUNKI NENKAI KOEN YOKOSHU II, 12 March 2007 (2007-03-12), pages 1231, XP008143259 *
See also references of EP2184290A4
TRENDS IN BIOCHEMICAL SCIENCES, vol. 27, no. 3, March 2002 (2002-03-01)
ZHANG R. ET AL.: "Probing the substrate specificity of Hepatitis C Virus NS3 serine protease by using synthetic peptides", J. VIROL., vol. 71, no. 8, 1997, pages 6208 - 6213, XP008129805 *
ZHU X. ET AL.: "Synthesis of an S-linked glycopeptides analog derived from human Tamm-Horsfall glycoprotein", ORG. BIOMOL. CHEM., vol. 2, no. 1, 2004, pages 31 - 33, XP003010443 *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010538063A (ja) * 2007-09-04 2010-12-09 イプセン ファルマ ソシエテ パール アクシオン サンプリフィエ ポリペプチドおよび蛋白質の化学的合成のための方法および中間体
WO2010092943A1 (ja) 2009-02-10 2010-08-19 大塚化学株式会社 IgG-Fcフラグメント及びその製造方法
JP5575670B2 (ja) * 2009-02-10 2014-08-20 株式会社糖鎖工学研究所 ＩｇＧ−Ｆｃフラグメント及びその製造方法
WO2010133382A3 (de) * 2009-05-20 2011-09-29 Henkel Ag & Co. Kgaa Kosmetische zusammensetzung und verformungsverfahren für keratinische fasern
WO2013047846A1 (ja) 2011-10-01 2013-04-04 株式会社糖鎖工学研究所 糖鎖付加ポリペプチドおよび当該ポリペプチドを含む医薬組成物
JPWO2013047846A1 (ja) * 2011-10-01 2015-03-30 株式会社糖鎖工学研究所 糖鎖付加ポリペプチドおよび当該ポリペプチドを含む医薬組成物
US10358470B2 (en) 2011-10-01 2019-07-23 Glytech, Inc. Glycosylated polypeptide and pharmaceutical composition containing same
US10053499B2 (en) 2013-03-29 2018-08-21 Glytech, Inc. Polypeptide having sialylated sugar chains attached thereto

Also Published As

Publication number Publication date
TW200918551A (en) 2009-05-01
KR20100065295A (ko) 2010-06-16
CN101796064B (zh) 2014-04-16
DK2767545T3 (en) 2017-06-06
RU2010107283A (ru) 2011-09-10
EP2184290A4 (en) 2011-11-09
EP2767545B1 (en) 2017-03-15
US8809258B2 (en) 2014-08-19
US20110172392A1 (en) 2011-07-14
SG183068A1 (en) 2012-08-30
BRPI0813858B1 (pt) 2019-09-17
TWI405770B (zh) 2013-08-21
CN102850442B (zh) 2014-07-30
CA2694542A1 (en) 2009-02-05
JPWO2009017154A1 (ja) 2010-10-21
CN101796064A (zh) 2010-08-04
JP5517620B2 (ja) 2014-06-11
EP2184290B1 (en) 2015-02-18
EP2767545A1 (en) 2014-08-20
KR101534881B1 (ko) 2015-07-07
EP2184290A1 (en) 2010-05-12
RU2478105C2 (ru) 2013-03-27
CN102850442A (zh) 2013-01-02
US20140235822A1 (en) 2014-08-21
CA2694542C (en) 2017-08-29
AU2008283317A1 (en) 2009-02-05
DK2184290T3 (en) 2015-05-26
BRPI0813858A2 (pt) 2015-01-06
AU2008283317B2 (en) 2012-08-02

Similar Documents

Publication Publication Date Title
WO2009017154A1 (ja) ペプチドの製造方法
WO2010098629A3 (ko) 메칠머캅탄과 디메칠설파이드의 혼합물을 사용하여 메치오닌 생산능을 증가시키는 방법
WO2010013856A3 (en) Catalysts for nox reduction employing h2 and a method of reducing nox
WO2010125189A3 (fr) Procédé de préparation d'un substrat métallisé, ledit substrat et ses utilisations
UA95600C2 (en) Synthesis scheme for lacosamide
WO2007117500A3 (en) Processes for chemical synthesis of lipochitooligosaccharides
WO2007146143A3 (en) Processes for converting glycerol to amino alcohols
EP1561819A4 (en) METHOD FOR TRANSMITTING A GENE IN T CELLS
WO2008133164A1 (ja) アミノ末端1箇所で配向制御固定化された固定化タンパク質
WO2010058129A3 (fr) Procede de fabrication de methylmercaptopropionaldehyde et de methionine a partir de matieres premieres renouvelables
WO2011131532A3 (en) Method for the manufacture of an ammonium sulfate composition
WO2008066816A3 (en) Derivatization or ligaton of peptides
WO2009014176A1 (ja) ペプチドの製造方法
WO2009066735A1 (ja) ２－アザアダマンタン類の製造方法
WO2009125945A3 (ko) 포토레지스트 스트리퍼 조성물 및 이를 이용한 포토레지스트 박리방법
WO2009040646A3 (en) Hydrogen production method, hydrogen production system, and fuel cell system
MX2009009631A (es) Proceso para la preparacion de esteres metilicos de aminoacido.
WO2008078589A1 (ja) 放射性ハロゲン標識有機化合物の前駆体化合物の製造方法
WO2009004951A1 (ja) セルロースを含む材料の加水分解および酵素糖化による単糖類の製造方法
WO2010058983A3 (ko) (메트)아크릴산 에스테르의 회수방법
ZA200801577B (en) Method for preparing 4ß-Amino-4'-demethyl-4-desoxy-podophyllotoxin
WO2009005069A1 (ja) ルテニウム触媒を用いた重水素化方法
NZ605608A (en) Method of synthesis of ferroquine by convergent reductive amination
ZA201002727B (en) Process for a reduction in the amount of sulphur compounds, hydrogen cyanide and formic acid in synthesis gas
WO2009150363A3 (fr) Acide cyanhydrique contenant du carbone bioressource

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 200880101043.1

Country of ref document: CN

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

Ref document number: 08791890

Country of ref document: EP

Kind code of ref document: A1

WWE Wipo information: entry into national phase

Ref document number: 2008283317

Country of ref document: AU

WWE Wipo information: entry into national phase

Ref document number: 2694542

Country of ref document: CA

ENP Entry into the national phase

Ref document number: 2009525431

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

ENP Entry into the national phase

Ref document number: 2008283317

Country of ref document: AU

Date of ref document: 20080730

Kind code of ref document: A

WWE Wipo information: entry into national phase

Ref document number: 1013/CHENP/2010

Country of ref document: IN

WWE Wipo information: entry into national phase

Ref document number: 2008791890

Country of ref document: EP

ENP Entry into the national phase

Ref document number: 20107004198

Country of ref document: KR

Kind code of ref document: A

WWE Wipo information: entry into national phase

Ref document number: 2010107283

Country of ref document: RU

WWE Wipo information: entry into national phase

Ref document number: 12671238

Country of ref document: US

ENP Entry into the national phase

Ref document number: PI0813858

Country of ref document: BR

Kind code of ref document: A2

Effective date: 20100128