Preparation of peptide thioesters using Fmoc-solid-phase peptide synthesis and its application to the construction of a template-assembled synthetic protein (TASP)

被引:111
|
作者
Futaki, S [1 ]
Sogawa, K [1 ]
Maruyama, J [1 ]
Asahara, T [1 ]
Niwa, M [1 ]
Hojo, H [1 ]
机构
[1] OSAKA CITY UNIV,FAC ENGN,DEPT BIOAPPL CHEM,SUMIYOSHI KU,OSAKA 558,JAPAN
关键词
D O I
10.1016/S0040-4039(97)01434-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Preparation of peptide thioesters was conducted through peptide chain construction with Fmoc-solid-phase peptide synthesis on a 2-chlorotrityl resin followed by coupling with HS-(CH2)(2)-COOEt and deprotection with 95% aqueous CF3COOH. The peptide thioester corresponding to a transmembrane segment of he calcium channel (S4 in repeat IV) thus obtained was introduced onto a peptide template to give an artificial four-helix-bundle protein. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:6237 / 6240
页数:4
相关论文
共 50 条
  • [21] Preparation and Application of an Inexpensive ?-Formylglycine Building Block Compatible with Fmoc Solid-Phase Peptide Synthesis
    Yates, Nicholas D. J.
    Warnes, Matthew E.
    Breetveld, Reuben
    Spicer, Christopher D.
    Signoret, Nathalie
    Fascione, Martin
    ORGANIC LETTERS, 2023, 25 (12) : 2001 - 2005
  • [22] Fmoc solid-phase synthesis of C-terminal peptide thioesters by formation of a pyroglutamyl imide moiety
    Tofteng, A. Pernille
    Conde-Frieboes, Kilian W.
    Hoeg-Jensen, Thomas
    Jensen, Knud J.
    JOURNAL OF PEPTIDE SCIENCE, 2008, 14 (08) : 15 - 15
  • [23] A new Fmoc-compatible method for the solid-phase synthesis of peptide C-terminal α-thioesters
    Camarero, JA
    de Yoreo, J
    Mitchell, AR
    BIOPOLYMERS, 2003, 71 (03) : 363 - 363
  • [24] FMOC SOLID-PHASE SYNTHESIS OF C-TERMINAL PEPTIDE THIOESTERS BY FORMATION OF A PYROGLUTAMYL IMIDE MOIETY
    Tofteng, A. P.
    Sorensen, K.
    Conde-Frieboes, K.
    Hoeg-Jensen, T. S.
    Jensen, K.
    BIOPOLYMERS, 2009, 92 (04) : 321 - 321
  • [25] New strategy for fmoc solid-phase synthesis of peptide thioesters: Masking of the thioester as a trithio ortho ester
    Brask, J
    Albericio, F
    Jensen, KJ
    BIOPOLYMERS, 2003, 71 (03) : 347 - 347
  • [26] PREPARATION OF A TERTIARYALKYLOXYCARBONYL HYDRAZIDE RESIN AND ITS APPLICATION TO SOLID PHASE PEPTIDE SYNTHESIS
    WANG, SS
    MERRIFIE.RB
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1969, (SEP): : B216 - &
  • [27] PREPARATION AND APPLICATION OF NEW ACID LABILE ANCHOR GROUPS FOR THE SYNTHESIS OF PEPTIDE AMIDES BY FMOC SOLID-PHASE SYNTHESIS
    BREIPOHL, G
    KNOLLE, J
    STUBER, W
    TETRAHEDRON LETTERS, 1987, 28 (46) : 5651 - 5654
  • [28] Automated Fmoc-Based Solid-Phase Synthesis of Peptide Thioesters with Self-Purification Effect and Application in the Construction of Immobilized SH3 Domains
    Mende, Franziska
    Beisswenger, Michael
    Seitz, Oliver
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (32) : 11110 - 11118
  • [29] Fmoc solid-phase synthesis of C-terminal thioesters peptide using an intramolecular N,S-acyl shift
    Ollivier, N.
    Behr, J. B.
    El-Mahdi, O.
    Blanpain, A.
    Melnyk, O.
    JOURNAL OF PEPTIDE SCIENCE, 2006, 12 : 130 - 130
  • [30] TERA-linker: Safety-catch linker for peptide thioesters via Fmoc solid-phase synthesis
    Rasmussen, J. E.
    Hoeg-Jensen, T.
    Jensen, K. J.
    JOURNAL OF PEPTIDE SCIENCE, 2010, 16 : 72 - 73