Solid-phase synthesis of peptide selenoesters via a side-chain anchoring strategy

被引:27
|
作者
Hanna, Cameron C. [1 ]
Kulkarni, Sameer S. [1 ]
Watson, Emma E. [1 ]
Premdjee, Bhavesh [1 ]
Payne, Richard J. [1 ]
机构
[1] Univ Sydney, Sch Chem, Sydney, NSW 2006, Australia
基金
澳大利亚研究理事会;
关键词
NATIVE CHEMICAL LIGATION; PROTEIN-SYNTHESIS; OXIDATIVE DESELENIZATION; DESULFURIZATION; CYSTEINE; SELENOCYSTEINE; THIOESTERS; CHEMISTRY;
D O I
10.1039/c7cc00823f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Peptide selenoesters have recently emerged as key building blocks for the ligation-based assembly of large polypeptides and proteins. Herein, we report an efficient solid-phase method for the high yielding and epimerisation-free synthesis of peptide selenoesters using a side-chain immobilisation strategy.
引用
收藏
页码:5424 / 5427
页数:4
相关论文
共 50 条
  • [1] Side-chain anchoring strategy for solid-phase synthesis of peptide acids with C-terminal cysteine
    Barany, G
    Han, YX
    Hargittai, B
    Liu, RQ
    Varkey, JT
    [J]. BIOPOLYMERS, 2003, 71 (06) : 652 - 666
  • [2] Solid-phase synthesis:: a linker for side-chain anchoring of arginine
    García, O
    Nicolás, E
    Albericio, F
    [J]. TETRAHEDRON LETTERS, 2003, 44 (28) : 5319 - 5321
  • [3] Solid-Phase Synthesis of Macrocyclic Peptides via Side-Chain Anchoring of the Ornithine δ-Amine
    Peterse, Evert
    Meeuwenoord, Nico
    van den Elst, Hans
    van der Marel, Gijsbert A.
    Overkleeft, Hermen S.
    Filippov, Dmitri V.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (11)
  • [4] MINIMAL SIDE-CHAIN PROTECTION CAN BE A SUCCESSFUL STRATEGY IN SOLID-PHASE PEPTIDE-SYNTHESIS
    COY, DH
    BRANYAS, N
    [J]. INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH, 1979, 14 (04): : 339 - 343
  • [5] Solid-Phase Synthesis of Caged Luminescent Peptides via Side Chain Anchoring
    Sondag, Daan
    Heming, Jurriaan J. A.
    Lowik, Dennis W. P. M.
    Krivosheeva, Elena
    Lejeune, Denise
    van Geffen, Mark
    Van't Veer, Cornelis
    van Heerde, Waander L.
    Beens, Marjolijn C. J.
    Kuijpers, Brian H. M.
    Boltje, Thomas J.
    Rutjes, Floris P. J. T.
    [J]. BIOCONJUGATE CHEMISTRY, 2023, 34 (12) : 2234 - 2242
  • [6] SOLID-PHASE SYNTHESIS OF HEAD-TO-TAIL CYCLIC-PEPTIDES VIA LYSINE SIDE-CHAIN ANCHORING
    ALSINA, J
    RABANAL, F
    GIRALT, E
    ALBERICIO, F
    [J]. TETRAHEDRON LETTERS, 1994, 35 (51) : 9633 - 9636
  • [7] STABILITY OF SIDE-CHAIN PROTECTING GROUPS IN SOLID-PHASE PEPTIDE-SYNTHESIS
    ERICKSON, BW
    MERRIFIE.RB
    [J]. ISRAEL JOURNAL OF CHEMISTRY, 1974, 12 (1-2) : 79 - 85
  • [8] Solid-phase peptide synthesis (SPPS), C-terminal vs. side-chain anchoring: a reality or a myth
    Prabhakar Cherkupally
    Gerardo A. Acosta
    Suhas Ramesh
    Beatriz G. De la Torre
    Thavendran Govender
    Hendrik G. Kruger
    Fernando Albericio
    [J]. Amino Acids, 2014, 46 : 1827 - 1838
  • [9] 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
    [J]. AMINO ACIDS, 2014, 46 (08) : 1827 - 1838
  • [10] Exploring Side-Chain Diversity by Submonomer Solid-Phase Aza-Peptide Synthesis
    Sabatino, David
    Proulx, Caroline
    Klocek, Sophie
    Bourguet, Carine B.
    Boeglin, Damien
    Ong, Huy
    Lubell, William D.
    [J]. ORGANIC LETTERS, 2009, 11 (16) : 3650 - 3653