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A practical
synthe
si
s of a new bifunctional diketopiperazine (DKP)
scaffold
1, formally derived fromthe cyclization of
L-a
spartic acid and (
S)-2,3-diaminopropionic acid, i
s reported. DKP-
1 bear
s a carboxylicacid and an amino functionalitie
s in a ci
s relation
ship, which have been u
sed to grow peptide
sequence
s.Tetra-, penta-, and hexapeptidomimetic
sequence
s were prepared by
solution-pha
se peptide
synthe
si
s(Boc
strategy). Conformational analy
si
s of the
se derivative
s wa
s carried out by a combination of
1HNMR
spectro
scopy, IR
spectro
scopy, CD
spectro
scopy, and computer modeling, and reveal
s the formationof
s/gifchar
s/beta2.gif" BORDER=0 ALIGN="middle">-hairpin mimic
s involving 10-membered and 18-membered H-bonded ring
s and a rever
se turn of thegrowing peptide chain.