Novel design of bicyclic β-turn dipeptides on solid-phase supports and synthesis of [3.3.0]-bicyclo[2,3]-leu-enkephalin analogues
(Chemical Equation Presented) External bicyclic β-turn dipeptide mimetics provide an excellent design approach that can offer a rich chiral ensemble of structures with different backbone conformations. We report herein a novel design of a convergent combinatorial synthetic methodology, which is illustrated by the solid-phase synthesis of a series of [3.3.0]-bicyclo [2,3]-Leu-enkephalin analogues. The reactions were optimized and the epimeric configurations were determined by 2D NMR spectroscopy. Biological assays show that these analogues have more potent δ binding affinity and bioactivity for δ vs μ opioid receptor, which may be related to the different conformations preferred by these analogues in our modeling studies.
Gu, Xuyuan,Ying, Jinfa,Agnes, Richard S.,Navratilova, Edita,Davis, Peg,Stahl, Gannon,Porreca, Frank,Yamamura, Henry I.,Hruby, Victor J.
p. 3285 - 3288
(2007/10/03)
Solid-phase approaches to regiospecific double disulfide formation. Application to a fragment of bovine pituitary peptide
A 21-residue, two disulfide-containing peptide has been synthesized on solid phase. Three alternative protection schemes, based on Boc/benzyl chemistry and combinations of the 4-methylbenzyl with either acetamidomethyl, 9-fluorenylmethyl or 3-nitro-2-pyridylsulfenyl groups for pairs of cysteine residues have been examined. The most successful route involved formation of the first disulfide on the resin via 9-fluorenylmethylcysteine deprotection-oxidation.
Ponsati, Berta,Giralt, Ernest,Andreu, David
p. 8255 - 8266
(2007/10/02)
More Articles about upstream products of 84888-38-0