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A new amino acid derivative with a masked side‐chain aldehyde and its use in peptide synthesis and chemoselective ligation
Author(s) -
Spetzler Jane C.,
HoegJensen Thomas
Publication year - 2001
Publication title -
journal of peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 66
eISSN - 1099-1387
pISSN - 1075-2617
DOI - 10.1002/psc.349
Subject(s) - aldehyde , peptide , chemistry , side chain , sodium periodate , combinatorial chemistry , oxime , amino acid , peptide synthesis , derivative (finance) , stereochemistry , organic chemistry , biochemistry , catalysis , polymer , financial economics , economics
A new amino acid derivative with a diol side‐chain, ‐2‐amino‐4,5‐dihydroxy‐pentanoic acid (Adi), has been prepared from ‐allylglycine by suitable protection, for use in peptide synthesis, as Fmoc‐‐Adi(Trt) 2 . This building block enables the introduction of a side‐chain aldehyde at any position in a given peptide sequence without use of specialized side‐chain protection schemes. The aldehyde is revealed by mild oxidation with sodium periodate, circumventing the problematic release of reactive peptidic aldehydes in TFA solution. Peptides with aldehyde side‐chains are useful for chemo‐selective ligation, reacting selectively with oxyamines to yield oxime links, while all other peptide functions can be left unprotected. The utility of the new building block has been demonstrated by the synthesis of peptide dimers and a cyclo‐peptide. Copyright © 2001 European Peptide Society and John Wiley & Sons, Ltd.