Amino Acid Building Blocks for Fmoc Solid-Phase Synthesis of Peptides Phosphocholinated at Serine, Threonine, and Tyrosine

被引:7
|
作者
Albers, Michael F. [1 ]
Hedberg, Christian [1 ]
机构
[1] Max Planck Inst Mol Physiol, Dept Biol Chem, D-44227 Dortmund, Germany
来源
JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 06期
关键词
RAB GTPASE FUNCTION; LEGIONELLA; PROTEINS;
D O I
10.1021/jo302587g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Phosphocholination of eukaryotic host cell proteins has recently been identified as a novel post-translational modification important for bacterial pathogenesis. Here, we describe the first straightforward synthetic strategy for peptides containing phosphocholinated serine, threonine, or tyrosine residues using preformed functional amino acid building blocks, fully compatible with standard Fmoc solid-phase peptide synthesis.
引用
收藏
页码:2715 / 2719
页数:5
相关论文
共 50 条
  • [1] Amino Acid Building Blocks for Efficient Fmoc Solid-Phase Synthesis of Peptides Adenylylated at Serine or Threonine
    Albers, Michael F.
    van Vliet, Bart
    Hedberg, Christian
    ORGANIC LETTERS, 2011, 13 (22) : 6014 - 6017
  • [2] PHOSPHO-SERINE AND PHOSPHO-THREONINE BUILDING-BLOCKS FOR THE SYNTHESIS OF PHOSPHORYLATED PEPTIDES BY THE FMOC SOLID-PHASE STRATEGY
    VORHERR, T
    BANNWARTH, W
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (22) : 2661 - 2664
  • [3] Solid-phase route to Fmoc-protected cationic amino acid building blocks
    Clausen, Jacob Dahlqvist
    Linderoth, Lars
    Nielsen, Hanne Morck
    Franzyk, Henrik
    AMINO ACIDS, 2012, 43 (04) : 1633 - 1641
  • [4] Solid-phase route to Fmoc-protected cationic amino acid building blocks
    Jacob Dahlqvist Clausen
    Lars Linderoth
    Hanne Mørck Nielsen
    Henrik Franzyk
    Amino Acids, 2012, 43 : 1633 - 1641
  • [5] Arylboronate Ester Protected Amino Acids as Orthogonal Building Blocks for Fmoc Solid-Phase Peptide Synthesis
    Liu, Chao
    Zou, Yan
    Song, Hui
    Jiang, Yuan-Ye
    Hu, Hong-Gang
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (39) : 5916 - 5920
  • [6] FMOC-AMINO ACID-CHLORIDES IN SOLID-PHASE SYNTHESIS OF OPIOID-PEPTIDES
    SIVANANDAIAH, KM
    BABU, VVS
    RENUKESHWAR, C
    INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH, 1992, 39 (03): : 201 - 206
  • [7] Preparation of N-Fmoc-protected β2- and β3-amino acids and their use as building blocks for the solid-phase synthesis of β-peptides
    Guichard, G
    Abele, S
    Seebach, D
    HELVETICA CHIMICA ACTA, 1998, 81 (02) : 187 - 206
  • [8] Caged phospho-amino acid building blocks for solid-phase peptide synthesis
    Rothman, DM
    Vazquez, ME
    Vogel, EM
    Imperiali, B
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (17): : 6795 - 6798
  • [9] Handles for Fmoc Solid-Phase Synthesis of Protected Peptides
    Gongora-Benitez, Miriam
    Tulla-Puche, Judit
    Albericio, Fernando
    ACS COMBINATORIAL SCIENCE, 2013, 15 (05) : 217 - 228
  • [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