257288-48-5Relevant articles and documents
Solid-phase approaches to regiospecific double disulfide formation. Application to a fragment of bovine pituitary peptide
Ponsati, Berta,Giralt, Ernest,Andreu, David
, p. 8255 - 8266 (1990)
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.
Novel design of bicyclic β-turn dipeptides on solid-phase supports and synthesis of [3.3.0]-bicyclo[2,3]-leu-enkephalin analogues
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)
(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.
