JPS62281828A - アミノ酸類またはペプチド類の保護基を除去する方法 - Google Patents

アミノ酸類またはペプチド類の保護基を除去する方法

Info

Publication number: JPS62281828A
Authority: JP; Japan
Prior art keywords: amino acid; lower alkyl; groups; peptide; group
Prior art date: 1986-05-29
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.): Granted

Application number

JP61122279A

Other languages

English (en)

Japanese (ja)

Other versions

JPH047731B2 (fr

Inventor

Hiroshi Yoshino

博吉野

Isao Saito

勲斉藤

Masahiko Tsujii

昌彦辻井

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.)

Eisai Co Ltd

Original Assignee

Eisai 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.)

1986-05-29

Filing date

1986-05-29

Publication date

1987-12-07

1986-05-29 Application filed by Eisai Co Ltd filed Critical Eisai Co Ltd

1986-05-29 Priority to JP61122279A priority Critical patent/JPS62281828A/ja

1987-12-07 Publication of JPS62281828A publication Critical patent/JPS62281828A/ja

1992-02-12 Publication of JPH047731B2 publication Critical patent/JPH047731B2/ja

Status Granted legal-status Critical Current

Links

150000001413 amino acids Chemical class 0.000 title claims abstract description 26
108090000765 processed proteins & peptides Proteins 0.000 title claims abstract description 17
125000006239 protecting group Chemical group 0.000 title claims abstract description 13
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims abstract description 24
238000000034 method Methods 0.000 claims abstract description 17
125000000217 alkyl group Chemical group 0.000 claims abstract description 12
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims abstract description 10
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims abstract description 10
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims abstract description 8
150000001555 benzenes Chemical class 0.000 claims abstract description 8
AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims abstract description 6
AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims abstract description 6
239000004473 Threonine Substances 0.000 claims abstract description 6
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims abstract description 6
MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims abstract description 5
MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims abstract description 5
AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims abstract description 4
239000004472 Lysine Substances 0.000 claims abstract description 4
AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims abstract description 4
UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims abstract description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
229960003104 ornithine Drugs 0.000 claims abstract description 4
102000004196 processed proteins & peptides Human genes 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 1
239000003223 protective agent Substances 0.000 claims 1
239000000126 substance Substances 0.000 claims 1
-1 tyrosine Chemical class 0.000 abstract description 5
125000003277 amino group Chemical group 0.000 abstract description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 2
238000007086 side reaction Methods 0.000 abstract description 2
239000012351 deprotecting agent Substances 0.000 abstract 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 12
238000010511 deprotection reaction Methods 0.000 description 12
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
BEZDDPMMPIDMGJ-UHFFFAOYSA-N pentamethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1C BEZDDPMMPIDMGJ-UHFFFAOYSA-N 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
KAFHLONDOVSENM-HNNXBMFYSA-N O-Benzyl-L-tyrosine Chemical compound C1=CC(C[C@H](N)C(O)=O)=CC=C1OCC1=CC=CC=C1 KAFHLONDOVSENM-HNNXBMFYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 6
239000005711 Benzoic acid Substances 0.000 description 4
ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 4
235000010233 benzoic acid Nutrition 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 3
JXNRXNCCROJZFB-RYUDHWBXSA-N Tyr-Arg Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@@H](N)CC1=CC=C(O)C=C1 JXNRXNCCROJZFB-RYUDHWBXSA-N 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
229910000040 hydrogen fluoride Inorganic materials 0.000 description 3
230000003287 optical effect Effects 0.000 description 3
238000010647 peptide synthesis reaction Methods 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
238000003756 stirring Methods 0.000 description 3
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
125000000524 functional group Chemical group 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
239000000047 product Substances 0.000 description 2
HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 2
FULCCCZBEUTMED-AWEZNQCLSA-N (2s)-2-amino-3-(3-benzyl-4-hydroxyphenyl)propanoic acid Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(CC=2C=CC=CC=2)=C1 FULCCCZBEUTMED-AWEZNQCLSA-N 0.000 description 1
CKGCFBNYQJDIGS-LBPRGKRZSA-N (2s)-2-azaniumyl-6-(phenylmethoxycarbonylamino)hexanoate Chemical compound [O-]C(=O)[C@@H]([NH3+])CCCCNC(=O)OCC1=CC=CC=C1 CKGCFBNYQJDIGS-LBPRGKRZSA-N 0.000 description 1
CNBUSIJNWNXLQQ-NSHDSACASA-N (2s)-3-(4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H](C(O)=O)CC1=CC=C(O)C=C1 CNBUSIJNWNXLQQ-NSHDSACASA-N 0.000 description 1
CTXPLTPDOISPTE-YPMHNXCESA-N (2s,3r)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylmethoxybutanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H](C(O)=O)[C@@H](C)OCC1=CC=CC=C1 CTXPLTPDOISPTE-YPMHNXCESA-N 0.000 description 1
QQOMQLYQAXGHSU-UHFFFAOYSA-N 2,3,6-Trimethylphenol Chemical compound CC1=CC=C(C)C(O)=C1C QQOMQLYQAXGHSU-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
JXNRXNCCROJZFB-UHFFFAOYSA-N Di-Me ester-(2R, 3E)-Phytochromobilin Natural products NC(N)=NCCCC(C(O)=O)NC(=O)C(N)CC1=CC=C(O)C=C1 JXNRXNCCROJZFB-UHFFFAOYSA-N 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
108010065372 Dynorphins Proteins 0.000 description 1
108010092674 Enkephalins Proteins 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
URLZCHNOLZSCCA-VABKMULXSA-N Leu-enkephalin Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)CNC(=O)CNC(=O)[C@@H](N)CC=1C=CC(O)=CC=1)C1=CC=CC=C1 URLZCHNOLZSCCA-VABKMULXSA-N 0.000 description 1
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
102100029251 Phagocytosis-stimulating peptide Human genes 0.000 description 1
102100024622 Proenkephalin-B Human genes 0.000 description 1
108010084754 Tuftsin Proteins 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000003862 amino acid derivatives Chemical class 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
244000309464 bull Species 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000001735 carboxylic acids Chemical group 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
235000009508 confectionery Nutrition 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000006264 debenzylation reaction Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000001514 detection method Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
108010053037 kyotorphin Proteins 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
CWWARWOPSKGELM-SARDKLJWSA-N methyl (2s)-2-[[(2s)-2-[[2-[[(2s)-2-[[(2s)-2-[[(2s)-5-amino-2-[[(2s)-5-amino-2-[[(2s)-1-[(2s)-6-amino-2-[[(2s)-1-[(2s)-2-amino-5-(diaminomethylideneamino)pentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-5 Chemical compound C([C@@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)OC)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CCCN=C(N)N)C1=CC=CC=C1 CWWARWOPSKGELM-SARDKLJWSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
VHNBNECUVQXBQA-UHFFFAOYSA-N methylsulfanylbenzene;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CSC1=CC=CC=C1 VHNBNECUVQXBQA-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000009965 odorless effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
UOHMMEJUHBCKEE-UHFFFAOYSA-N prehnitene Chemical compound CC1=CC=C(C)C(C)=C1C UOHMMEJUHBCKEE-UHFFFAOYSA-N 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical group CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
IESDGNYHXIOKRW-LEOABGAYSA-N tuftsin Chemical compound C[C@@H](O)[C@H](N)C(=O)N[C@@H](CCCCN)C(=O)N1CCC[C@H]1C(=O)N[C@H](CCCNC(N)=N)C(O)=O IESDGNYHXIOKRW-LEOABGAYSA-N 0.000 description 1
229940035670 tuftsin Drugs 0.000 description 1

Classifications

- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Peptides Or Proteins (AREA)

JP61122279A 1986-05-29 1986-05-29 アミノ酸類またはペプチド類の保護基を除去する方法 Granted JPS62281828A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP61122279A JPS62281828A (ja)	1986-05-29	1986-05-29	アミノ酸類またはペプチド類の保護基を除去する方法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP61122279A JPS62281828A (ja)	1986-05-29	1986-05-29	アミノ酸類またはペプチド類の保護基を除去する方法

Publications (2)

Publication Number	Publication Date
JPS62281828A true JPS62281828A (ja)	1987-12-07
JPH047731B2 JPH047731B2 (fr)	1992-02-12

Family

ID=14832025

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP61122279A Granted JPS62281828A (ja)	1986-05-29	1986-05-29	アミノ酸類またはペプチド類の保護基を除去する方法

Country Status (1)

Country	Link
JP (1)	JPS62281828A (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH05194279A (ja) *	1991-10-11	1993-08-03	Rhone Poulenc Chim	アルコキシカルボニル基により保護されている官能基の開裂用試薬
WO2009142204A1 (fr) *	2008-05-21	2009-11-26	日産化学工業株式会社	Agent générateur d’acide aminé et composition de polysiloxane contenant ledit agent

1986
- 1986-05-29 JP JP61122279A patent/JPS62281828A/ja active Granted

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH05194279A (ja) *	1991-10-11	1993-08-03	Rhone Poulenc Chim	アルコキシカルボニル基により保護されている官能基の開裂用試薬
WO2009142204A1 (fr) *	2008-05-21	2009-11-26	日産化学工業株式会社	Agent générateur d’acide aminé et composition de polysiloxane contenant ledit agent
CN102037092A (zh) *	2008-05-21	2011-04-27	日产化学工业株式会社	氨基酸产生剂和含有氨基酸产生剂的聚硅氧烷组合物
JPWO2009142204A1 (ja) *	2008-05-21	2011-09-29	日産化学工業株式会社	アミノ酸発生剤及びそれを含むポリシロキサン組成物
JP2015110774A (ja) *	2008-05-21	2015-06-18	日産化学工業株式会社	アミノ酸発生剤を含むポリシロキサン組成物
US9257576B2 (en)	2008-05-21	2016-02-09	Nissan Chemical Industries, Ltd.	Amino acid generator and polysiloxane composition containing the same
TWI550076B (zh) *	2008-05-21	2016-09-21	日產化學工業股份有限公司	胺基酸產生劑及含有該胺基酸產生劑之聚矽氧烷組成物

Also Published As

Publication number	Publication date
JPH047731B2 (fr)	1992-02-12

Publication	Publication Date	Title
EP0144103B1 (fr)	1993-12-29	Méthodes et composés pour la préparation de H-ARG-X-Z-Y-TYR-R
JPS58116443A (ja)	1983-07-11	新規ペプチドおよびその製法
Li et al.	1960	The Synthesis of L-Histidyl-L-phenylalanyl-L-ornithyl-L-tryptophyl-glycine and L-Histidyl-D-phenylalanyl-L-ornithyl-L-tryptophyl-glycine and their Melanocyte-stimulating Activity
SE452318B (sv)	1987-11-23	Aminosyror till anvendning som mellanprodukter vid framstellning av bestatiner
JPS62281828A (ja)	1987-12-07	アミノ酸類またはペプチド類の保護基を除去する方法
JPS6220200B2 (fr)	1987-05-06
JP2577730B2 (ja)	1997-02-05	細胞成長調節効果を有するペンタペプチド類およびその製造法
US4369137A (en)	1983-01-18	N-Protected pentapeptides useful as intermediates in the preparation of thymopoietin pentapeptide
JPS5850982B2 (ja)	1983-11-14	ペプチド
WO1995024421A1 (fr)	1995-09-14	Derive peptidique
US3433779A (en)	1969-03-18	Long-chain aliphatic esters of lysine and other basic amino acids and peptides thereof
JP3657118B2 (ja)	2005-06-08	テアニンの製造方法
US4389342A (en)	1983-06-21	Synthetic hormone-like peptides and method for their synthesis
JPH0381289A (ja)	1991-04-05	新規迅速ペプチドカップリング法
JPH08119916A (ja)	1996-05-14	Ｎ−保護グルタミン酸γ−誘導体の選択的製造法
JPS59219259A (ja)	1984-12-10	ゴナドリベリン誘導体
JPS5874643A (ja)	1983-05-06	アミノ酸クロリドの製造法
JPH01197465A (ja)	1989-08-09	新規アルギニン誘導体、その製法及びペプチド合成における使用法
JPS6136298A (ja)	1986-02-20	トリペプチドアミド類
Fletcher et al.	1973	Amino-acids and peptides. Part XXXVII. Trifluoroacetylation during the coupling of t-butoxycarbonylamino-acids with peptide esters in the presence of trifluoroacetate anion
EP1440977B1 (fr)	2006-07-26	Procédé de synthèse amélioré de dérivés diamides du tripeptide KPV
JPH07316193A (ja)	1995-12-05	ペプチド誘導体およびその用途
JP3554399B2 (ja)	2004-08-18	ペプチド誘導体
US3585180A (en)	1971-06-15	Process for preparing peptides containing histidine protected with a 2,2,2,-trihalogeno - n -benzyloxycarbonylaminoethyl group
JPS60116700A (ja)	1985-06-24	キョ−トルフィン誘導体