Abstract
Practical methodology is reported for the synthesis of a homologous
series of side-chain-extended amino acids containing aminooxy functionality
bearing orthogonal protection suitable for Fmoc peptide synthesis.
These reagents may be useful for the preparation of libraries containing
fragments joined by peptide linkers.
Key words
oxime - peptidomimetic - aldehydes - combinatorial chemistry
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17 The major fraction obtained by HPLC
purification of the peptide resulting using 1a to
replace the Thr residue, provided a mass spectral molecular ion
(m/z = 1422.4)
that was 31 amu lower than expected for the correct product
(m/z = 1453.5).
This is consistent with β-elimination of HONH2 followed
by reduction of the resulting double bond during under the reducing
conditions of resin cleavage using triethylsilane.
18 The major fraction obtained by HPLC
purification of the peptide resulting from the use of 2a to replace the Thr residue, provided
mass spectral molecular ions consistent with the desired peptide
product [m/z = 1454.5, (M + H)
and 1476.5 (M + Na)].
