IMPROVED SOLID-PHASE SYNTHESIS OF C-TERMINAL PEPTIDE ALDEHYDES

被引:80
|
作者
FEHRENTZ, JA
PARIS, M
HEITZ, A
VELEK, J
LIU, CF
WINTERNITZ, F
MARTINEZ, J
机构
[1] FAC PHARM MONTPELLIER,CNRS,CHIM & PHARMACOL MOLECULES INTERET BIOL LAB,F-34060 MONTPELLIER,FRANCE
[2] FAC PHARM MONTPELLIER,CNRS,UNITE MIXTE,F-34060 MONTPELLIER,FRANCE
关键词
D O I
10.1016/0040-4039(95)01646-Y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new linker based on the Weinreb amide was developed in order to synthesize from peptidyl-resin the corresponding aldehydic peptides by reduction with LiAlH4. This new reaction was tested with N-protected amino-residues and with tripeptides to obtain the corresponding aldehydes without racemisation.
引用
收藏
页码:7871 / 7874
页数:4
相关论文
共 50 条
  • [41] SOLID-PHASE SYNTHESIS OF A GHRP ANALOG CONTAINING C-TERMINAL THIOAMIDE GROUP
    MAJER, Z
    ZEWDU, M
    HOLLOSI, M
    SEPRODI, J
    VADASZ, Z
    TEPLAN, I
    BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1988, 150 (03) : 1017 - 1020
  • [42] Solid-phase synthesis of peptide isosters by nucleophilic reactions with N-terminal peptide aldehydes on a polar support tailored for solid-phase organic chemistry
    Rademann, J
    Meldal, M
    Bock, K
    CHEMISTRY-A EUROPEAN JOURNAL, 1999, 5 (04) : 1218 - 1225
  • [43] SOLID-PHASE SYNTHESIS OF C-TERMINAL HEXAPEPTIDE ANALOGS OF SUBSTANCE-P
    SOFUKU, S
    ISHIKAWA, A
    MURAMATSU, I
    SHIBATA, K
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (09) : 3374 - 3376
  • [44] Facile Synthesis of Internal and C-Terminal Peptide α-Ketoamides with Fmoc-Solid Phase Peptide Synthesis
    Rohrbacher, Florian
    Zwicky, Andre
    Bode, Jeffrey W.
    HELVETICA CHIMICA ACTA, 2018, 101 (05)
  • [45] Solid-phase synthesis of peptide aldehydes directly on acetal resin
    Yao, W
    Xu, HY
    TETRAHEDRON LETTERS, 2001, 42 (13) : 2549 - 2552
  • [46] A simple oxazolidine linker for solid-phase synthesis of peptide aldehydes
    Kang, Wu
    Wang, Weiguo
    Zhi, XiaoXia
    Zhang, Bo
    Wei, Ping
    Xu, HongYan
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (02) : 1187 - 1188
  • [47] A new linker for the synthesis of C-terminal peptide α-oxo-aldehydes
    Fruchart, JS
    Gras-Masse, H
    Melnyk, O
    TETRAHEDRON LETTERS, 1999, 40 (34) : 6225 - 6228
  • [48] Solid-phase peptide synthesis (SPPS), C-terminal vs. side-chain anchoring: a reality or a myth
    Cherkupally, Prabhakar
    Acosta, Gerardo A.
    Ramesh, Suhas
    De la Torre, Beatriz G.
    Govender, Thavendran
    Kruger, Hendrik G.
    Albericio, Fernando
    AMINO ACIDS, 2014, 46 (08) : 1827 - 1838
  • [50] AN ACID-LABILE ANCHORING LINKAGE FOR SOLID-PHASE SYNTHESIS OF C-TERMINAL PEPTIDE AMIDES UNDER MILD CONDITIONS
    ALBERICIO, F
    BARANY, G
    INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH, 1987, 30 (02): : 206 - 216