Abstract: Ac-Phe-Tyr-phosphoSer-?[CH?C]-Pro-Arg-NH2AND Fmoc-bis(pivaloylmethoxy)phosphoSer-?[CH?C]-Pro-2-aminoethyl-(3-indole); and their Phospho-(D)-serine stereoisomers are novel compounds. ? refers to a pseudo amide. Such novel compounds advantageously may be used as alkene mimics.

Abstract: Novel peptidomimetics are provided, which mimic collagen. Molecular structures of interest include for imparting the collagen-mimicking property are each of: Gly-?[(E)CH?C]-Xaa-?[(E)CH?C]-Yaa; Gly-Xaa-?[(E)CH?C]-Yaa; Gly-Xaa-Yaa-?[(E)CH?CH]; Gly-?[(E)CH?C]-Xaa-?[(E)CH?C]-Yaa; Gly-Xaa-?(E)CH?C]-Yaa-?[(E)CH?CH]; Gly-?[(E)CH?C]-Xaa-Yaa-?[(E)CH?CH] and Gly-?[(E)CH?C]-Xaa-?[(E)CH?C]-Yaa-?[(E)CH?CH]. Xaa and Yaa each means a natural amino acid, Hyp or Flp. Amide bonds may be altered to create collagen mimics. Preferably a tripeptide polymer comprising at least about 60 (Gly-Pro-Hyp) repeating units and having molecular weight of at least about 40,000 is synthesized as a long, collagen-like material. The new synthetic collagen-like materials may have better resistance to degradation, better mechanical strength and/or better ability to fold than natural collagen.

Abstract: Novel ?-ketoamide-containing peptidomimetics are provided, such as peptidomimetics containing an ?-ketoamide Ser-Pro dipeptide analogue. The ?-ketoamide is preferably incorporated into another molecule as a Pin1 inhibitor (such as a pentapeptide analogue Ac-Phe-Tyr-pSer-Pro-Arg-NH2).

Abstract: A peptidomimetic of the turn in the helix-turn-helix (HTH) motif of DNA-binding proteins was designed and synthesized. Conformational constraint was achieved by an unusual linking of two amino acids with a side-chain carbon--carbon bond. A phenyl ring provides the potential for new hydrophobic contacts with the hydrophobic core of the HTH motif. In the mimic, the peptide backbone and the central residue were retained in native form within a 12-membered cyclic tripeptide. The target compound 1b was synthesized by two sequential Horner-Wittig couplings followed by enantioselective hydrogenation with Rh(MeDuPHOS) in 8 steps and 35% overall yield. The stereochemical outcome of the key hydrogenation was determined by aromatic ring oxidation with RuO.sub.2 /NalO.sub.4 to give two equivalents of Boc-Asp-OMe.