I. Torrini et al., Pseudopeptides containing the 2-hydrazonoacyl fragment: analogs of the chemotactic agent HCO-Met-Leu-Phe-OMe, J PEPT RES, 58(1), 2001, pp. 56-66
In order to further examine the properties of pseudopeptides containing the
2-hydrazonoacyl fragment, two new series of analogs of the prototypical ch
emotactic N-formyl-tripeptide HCO-Met-Leu-Phe-OMe were designed and synthes
ized. The first group contains the new fragment as the N-terminal residue a
nd is represented by the N-aryl derivatives p-Cl-C6H4-NH-N=C(R)-CO-Leu-Phe-
OMe (2 and 3) and by the corresponding N-aroyl analogs p-CH3-C6H4-CO-NH-N =
C(R)-CO-Leu-Phe-OMe (4). The second group contains the new fragment in pla
ce of the central Leu residue and is represented by compounds HCO-Xaa-NH-N=
C(R)-CO-Phe-OMe (7a and 7b) where Xaa is Nle and Met, respectively. The co
nformational and biochemical properties of the new products were examined.