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Chemical Synthesis of K48‐Linked Diubiquitin by Incorporation of a Lysine‐Linked Auxiliary Handle
Author(s) -
Xie RuiLong,
Xu Ling,
Li JiaBin,
Chu GuoChao,
Wang Tao,
Huang YiChao,
Li YiMing
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600292
Subject(s) - chemistry , chemical ligation , lysine , native chemical ligation , block (permutation group theory) , hydrazide , chemical synthesis , yield (engineering) , combinatorial chemistry , solid phase synthesis , stereochemistry , organic chemistry , peptide , amino acid , biochemistry , in vitro , materials science , geometry , mathematics , metallurgy
Abstract We synthesized a lysine‐linked auxiliary‐derived building block, ϵ‐ N ‐2‐mercapto‐1‐(2,4‐dimethoxyphenyl)ethyl lysine, in 20 % isolated yield over a six‐step route. The new building block is well compatible with Fmoc solid‐phase peptide synthesis (SPPS) and hydrazide‐based native chemical ligation (NCL). Furthermore, we successfully incorporated the new lysine‐linked auxiliary handle into a protein segment and performed the chemical synthesis of K48‐linked diubiquitin with stepwise NCL.