Chemical Synthesis of Peptides and Proteins Bearing Base-Labile Post-Translational Modifications: Evolution of the Methods in Four Decades

被引:6
作者
Ma, Wenjie [1 ]
Liu, Han [1 ]
Li, Xuechen [1 ]
机构
[1] Univ Hong Kong, Dept Chem, State Key Lab Synthet Chem, Pokfulam Rd, Hong Kong, Peoples R China
关键词
base-labile posttranslation modification; chemical protein synthesis; chemical ligation; S-palmitoylation; O-acetylation; SOLID-PHASE SYNTHESIS; MYELIN PROTEOLIPID PROTEIN; LIPID-MODIFIED PROTEINS; SAFETY-CATCH LINKER; N-RAS PROTEIN; CHEMOENZYMATIC SYNTHESIS; CHARACTERISTIC LIPOPEPTIDES; TERMINAL LIPOHEXAPEPTIDE; EFFICIENT SYNTHESIS; ENZYMATIC-SYNTHESIS;
D O I
10.1002/cbic.202300348
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
The S-palmitoylation on Cys residue and O-acetylation on Ser/Thr residues are two types of base-labile post-translational modifications (PTMs) in cells. The lability of these PTMs to bases and nucleophiles makes the peptides/proteins bearing S-palmitoyl or O-acetyl groups challenging synthetic targets, which cannot be prepared via the standard Fmoc-SPPS and native chemical ligation. In this review, we summarized the efforts towards their preparation in the past 40 years, with the focus on the evolution of synthetic methods.
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页数:12
相关论文
共 102 条
[51]   Serine/Threonine Ligation: Origin, Mechanistic Aspects, and Applications [J].
Liu, Han ;
Li, Xuechen .
ACCOUNTS OF CHEMICAL RESEARCH, 2018, 51 (07) :1643-1655
[52]   Enabling chemical protein (semi)synthesis via reducible solubilizing tags (RSTs) [J].
Liu, Jiamei ;
Wei, Tongyao ;
Tan, Yi ;
Liu, Heng ;
Li, Xuechen .
CHEMICAL SCIENCE, 2022, 13 (05) :1367-1374
[53]   The synthesis of acid- and base-labile lipopeptides on solid support [J].
Ludolph, B ;
Waldmann, H .
CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (15) :3683-3691
[54]   Solid-phase synthesis of lipidated peptides [J].
Ludolph, B ;
Eisele, F ;
Waldmann, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (21) :5954-5955
[55]   Solid-phase synthesis of palmitoylated and farnesylated lipopeptides employing the fluoride-labile PTMSEL linker [J].
Lumbierres, M ;
Palomo, JM ;
Kragol, G ;
Waldmann, H .
TETRAHEDRON LETTERS, 2006, 47 (16) :2671-2674
[56]   Solid-phase synthesis of lipidated peptides [J].
Lumbierres, M ;
Palomo, JM ;
Kragol, G ;
Roehrs, S ;
Müller, O ;
Waldmann, H .
CHEMISTRY-A EUROPEAN JOURNAL, 2005, 11 (24) :7405-7415
[57]   Chemical Synthesis of Proteins with Base-Labile Posttranslational Modifications Enabled by a Boc-SPPS Based General Strategy Towards Peptide C-Terminal Salicylaldehyde Esters [J].
Ma, Wenjie ;
Wu, Hongxiang ;
Liu, Sha ;
Wei, Tongyao ;
Li, Xiang David ;
Liu, Han ;
Li, Xuechen .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (01)
[58]  
Machauer R, 2000, ANGEW CHEM INT EDIT, V39, P1449, DOI 10.1002/(SICI)1521-3773(20000417)39:8<1449::AID-ANIE1449>3.0.CO
[59]  
2-A
[60]   Protein S-Palmitoylation: advances and challenges in studying a therapeutically important lipid modification [J].
Main, Alice ;
Fuller, William .
FEBS JOURNAL, 2022, 289 (04) :861-882