2‐(Pyridyl)ethyl Esters as Secure yet Readily Removable Polarophilic Carboxy‐Protection in Peptide Synthesis | Zendy

Kunz Horst | Zendy; Kneip Michael | Zendy

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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.

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