Peptidomimetic of helix-turn-helix or gamma-turn

Details Peptidomimetic of helix-turn-helix or gamma-turn Peptidomimetic of helix-turn-helix or gamma-turn

1997-11-25

2000-06-27

Tsang, Cecilia J.

Chemistry: natural resins or derivatives; peptides or proteins;

Peptides of 3 to 100 amino acid residues

25 or more amino acid residues in defined sequence

530317, 530333, 514 12, A61K 3800

Patent

active

060808381

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.

REFERENCES:
Travins, et al., "Design and Enantioselective Synthesis of a Peptidomimetic of the Turn in the Helix-Turn-Helix DNA-Binding Protein Motif" J. Org. Chem., 1997, 62, 8387-93, 1997.

Affiliated with

Also associated with

Rating

Peptidomimetic of helix-turn-helix or gamma-turn does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Peptidomimetic of helix-turn-helix or gamma-turn, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Peptidomimetic of helix-turn-helix or gamma-turn will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1785478