100665-24-5

Upstream product

• 118903-75-6 N-chloroacetyl-S-t-butylthio-L-cysteinyl-L-phenylalanyl-L-proline t-butyl ester 
• 118903-74-5 N-chloroacetyl-S-t-butylthio-L-cysteine 
• 30044-51-0 S-tert-butylmercapto-L-cysteine 
• 100-02-7 4-nitro-phenol 
• 118903-76-7 (S)-1-{(R)-2-[(R)-3-tert-Butyldisulfanyl-2-(2-chloro-acetylamino)-propionylamino]-3-phenyl-propionyl}-pyrrolidine-2-carboxylic acid 
• 118903-75-6 (S)-1-{(S)-2-[(S)-3-tert-Butyldisulfanyl-2-(2-chloro-acetylamino)-propionylamino]-3-phenyl-propionyl}-pyrrolidine-2-carboxylic acid tert-butyl ester 
• 64830-74-6 L-phenylalanyl-L-proline tert-butyl ester 
• 118903-76-7 (S)-1-{(S)-2-[(S)-3-tert-Butyldisulfanyl-2-(2-chloro-acetylamino)-propionylamino]-3-phenyl-propionyl}-pyrrolidine-2-carboxylic acid 

Relevant academic research and scientific papers

ENDOANNULAR INTERACTIONS IN CYSTEINE-CONTAINING CYCLOTRIPEPTIDES: ONE-STEP SYNTHESIS AND CRYSTAL STRUCTURE OF A TETRACYCLIC AZA-CYCLOL

Mild unmasking of the thiol group of the linear tripeptide N-chloroacetyl-S-t-butylthio-L-cysteinyl-L-phenylalanyl-L-proline p-nitrophenyl ester (8) with tributylphosphine in aqueous solution at room temperature gave, in one step, the tetrahedral adduct (aza-cyclol) (13).The same adduct was obtained starting from (R)-5-oxothiomorpholin-3-ylcarbonyl-L-phenylalanyl-L-proline p-nitrophenyl ester (12).The conformationally rigid polycyclic skeleton stabilizes the structure of the aza-cyclol (13) which is an example of a tetrahedral adduct derived from amide-amide interaction.Relevant conformational details, as revealed by an X-ray crystallographic analysis, are: the proline ring adopts a Cs-Cβendo conformation; the phenylalanine side-chain is extended towards its nitrogen; the proline Hα and hydroxylic hydrogen atom are in the characteristic planar W conformation.

CYCLIZATION UNDER MILD CONDITIONS OF CYSTEINE CONTAINING PEPTIDES

Cyclization of di- and tripeptides containing cysteine as N-terminal residue is reported.The preferred cyclization patterns and the nature of the products (diketopiperazine, aza-cyclol, peptide thiolactone) are discussed.