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Bis(4,6‐dimethoxy‐1,3,5‐triazin‐2‐yl) Ether as Coupling Reagent for Peptide Synthesis
Author(s) -
Jastrzabek Konrad,
Bednarek Przemyslaw,
Kolesinska Beata,
Kaminski Zbigniew J.
Publication year - 2013
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201200369
Subject(s) - chemistry , dabco , yield (engineering) , reagent , steric effects , triazine , ether , octane , organic chemistry , enantiomer , peptide synthesis , peptide , medicinal chemistry , combinatorial chemistry , materials science , metallurgy , biochemistry
Bis(4,6‐dimethoxy‐1,3,5‐triazin‐2‐yl) ether ( 4 ) was prepared by treatment of 2‐hydroxy‐4,6‐dimethoxy‐1,3,5‐triazine with 2‐chloro‐4,6‐dimethoxy‐1,3,5‐triazine in 61% yield. Ether 4 , isoelectronic with pyrocarbonates, was found capable to activate carboxylic acids in the presence of 1,4‐diazabicyclo[2.2.2]octane (DABCO) to yield, under mild reaction conditions, superactive triazine esters. Versatility of this new coupling reagent was confirmed by condensation of lipophilic and sterically hindered carboxylic acids with amines in 71–98% yield, and by synthesis of peptides, including those containing Aib‐Aib sequence, in solution with high yield and high enantiomeric purity.