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2‐(Pyridyl)ethyl Esters as Secure yet Readily Removable Polarophilic Carboxy‐Protection in Peptide Synthesis
Author(s) -
Kunz Horst,
Kneip Michael
Publication year - 1984
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198407161
Subject(s) - morpholine , chemistry , peptide , protecting group , pyridinium , ethyl ester , cleavage (geology) , peptide synthesis , amino acid , stereochemistry , base (topology) , methylation , combinatorial chemistry , biochemistry , organic chemistry , dna , biology , mathematical analysis , alkyl , mathematics , fracture (geology) , paleontology
Pet (pyridyl‐ethyl ester) signifies two advantageous novel carboxy‐protecting groups for peptide synthesis. 2‐(2‐Pyridyl)‐ and 2‐(4‐pyridyl)ethyl esters of amino acids and peptides are both acid‐stable as well as relatively base‐stable; thus, they survive the acidolytic cleavage of the Z‐ and the Boc‐protecting group. After methylation to the extremely base‐labile pyridinium form (e.g. 1 ), Pet esters can be mildly cleaved with morpholine.