2-STEP HARD ACID DEPROTECTION CLEAVAGE PROCEDURE FOR SOLID-PHASE PEPTIDE-SYNTHESIS

被引：0
|
作者：
NOMIZU, M
INAGAKI, Y
YAMASHITA, T
OHKUBO, A
OTAKA, A
FUJII, N
ROLLER, PP
YAJIMA, H
机构：
[1] KIRIN BREWERY CO LTD,CENT LABS KEY TECHNOL,MAEBASHI,GUNMA,JAPAN
[2] KIRIN BREWERY CO LTD,PHARMACEUT LAB,MAEBASHI,GUNMA,JAPAN
[3] KYOTO UNIV,FAC PHARMACEUT SCI,KYOTO 606,JAPAN
来源：
INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH | 1991年 / 37卷 / 02期
关键词：
HUMAN ENDOTHELIN; HF; NIN-FORMYLTRYPTOPHAN; SOLID PHASE PEPTIDE SYNTHESIS; TRIMETHYLSILYL BROMIDE (TMSBR); TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE (TMSOTF); 2-STEP HARD ACID DEPROTECTION CLEAVAGE PROCEDURE; UROTENSIN-II;
D O I：
暂无
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
A new two-step deprotection/cleavage procedure for t-butoxycarbonyl (Boc) based solid phase peptide synthesis is reported. First the protective groups are removed from 4-(oxymethyl)-phenylacetamidomethyl (PAM) resin attached peptide with the weak hard acid, trimethylsilyl bromide-thioanisole/trifluoroacetic acid (TFA). In the second step, the peptide is cleaved from the resin with a stronger hard acid such as trimethylsilvl trifluoromethanesulfonate in TFA or with HF. The method is also shown to deformylate N(in)-formyltryptophan moiety efficiently. The usefulness of this procedure for practical solid phase peptide synthesis is demonstrated by comparison with other deprotection methods in the synthesis of urotensin II and human endothelin.
引用
收藏
页码：145 / 152
页数：8
相关论文
共 50 条
  • [1] SOLID-PHASE PEPTIDE-SYNTHESIS OF HUMAN ENDOTHELIN PRECURSOR PEPTIDES USING 2-STEP HARD ACID DEPROTECTION CLEAVAGE METHODS
    NOMIZU, M
    INAGAKI, Y
    IWAMATSU, A
    KASHIWABARA, T
    OHTA, H
    MORITA, A
    NISHIKORI, K
    OTAKA, A
    FUJII, N
    ROLLER, PP
    INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH, 1991, 38 (06): : 580 - 587
  • [2] SOLID-PHASE PEPTIDE-SYNTHESIS ON PROTEINS
    HANSEN, PR
    HOLM, A
    HOUEN, G
    INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH, 1993, 41 (03): : 237 - 245
  • [3] CONDUCTANCE MEASUREMENTS IN SOLID-PHASE PEPTIDE-SYNTHESIS .1. MONITORING COUPLING AND DEPROTECTION IN FMOC CHEMISTRY
    MCFERRAN, NV
    WALKER, B
    MCGURK, CD
    SCOTT, FC
    INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH, 1991, 37 (05): : 382 - 387
  • [4] AUTOMATIC SYNCHROM SYSTEM FOR SOLID-PHASE PEPTIDE-SYNTHESIS AND LIQUID COLUMN CHROMATOGRAPHY .2. APPLICATION TO SOLID-PHASE PEPTIDE-SYNTHESIS AND LIQUID COLUMN CHROMATOGRAPHY
    BARU, MB
    CHERSKII, VV
    DANILOV, AV
    MOSHNIKOV, SA
    MUSTAEVA, LG
    BIOORGANICHESKAYA KHIMIYA, 1995, 21 (07): : 506 - 516
  • [5] SOLID-PHASE PEPTIDE-SYNTHESIS OF SELECTIVELY PHOSPHORYLATED PEPTIDES
    STAERKAER, G
    JAKOBSEN, MH
    OLSEN, CE
    HOLM, A
    TETRAHEDRON LETTERS, 1991, 32 (39) : 5389 - 5392
  • [6] DIFFICULT SEQUENCES AND SOLVATION OF PEPTIDE CHAINS IN SOLID-PHASE PEPTIDE-SYNTHESIS
    NARITA, M
    OUCHI, S
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1994, 52 (08) : 686 - 697
  • [7] A NEW APPROACH TO THE SOLID-PHASE PEPTIDE-SYNTHESIS OF PEPTIDE ALKYL-AMIDES AND ESTERS
    NICOLAS, E
    CLEMENTE, J
    PERELLO, M
    ALBERICIO, F
    PEDROSO, E
    GIRALT, E
    TETRAHEDRON LETTERS, 1992, 33 (16) : 2183 - 2186
  • [8] DIFFICULT COUPLINGS IN STEPWISE SOLID-PHASE PEPTIDE-SYNTHESIS - PREDICTABLE OR JUST A GUESS
    VANWOERKOM, WJ
    VANNISPEN, JW
    INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH, 1991, 38 (02): : 103 - 113
  • [9] SOLID-PHASE PEPTIDE-SYNTHESIS ON HYDROPHILIC SUPPORTS .2. STUDIES USING PERLOZA BEADED CELLULOSE
    ENGLEBRETSEN, DR
    HARDING, DRK
    INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH, 1992, 40 (06): : 487 - 496
  • [10] INCOMPLETE FMOC DEPROTECTION IN SOLID-PHASE SYNTHESIS OF PEPTIDES
    LARSEN, BD
    HOLM, A
    INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH, 1994, 43 (01): : 1 - 9
12345