118903-75-6

Basic information

• Product Name: N-chloroacetyl-S-t-butylthio-L-cysteinyl-L-phenylalanyl-L-proline t-butyl ester
• CAS NO: 118903-75-6
• Molecular Weight: 586.217
• Mol File: 118903-75-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: N-chloroacetyl-S-t-butylthio-L-cysteinyl-L-phenylalanyl-L-proline t-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-chloroacetyl-S-t-butylthio-L-cysteinyl-L-phenylalanyl-L-proline t-butyl ester(118903-75-6)
• EPA Substance Registry System: N-chloroacetyl-S-t-butylthio-L-cysteinyl-L-phenylalanyl-L-proline t-butyl ester(118903-75-6)

Safety Data

• Hazardous Substances Data: 118903-75-6(Hazardous Substances Data)

Upstream product

• 30044-51-0 S-tert-butylmercapto-L-cysteine 
• 118903-74-5 N-chloroacetyl-S-t-butylthio-L-cysteine 
• 118903-81-4 L-phenylalanyl-L-proline t-butyl ester trifluoroacetate 
• 64830-74-6 L-phenylalanyl-L-proline tert-butyl ester 

Downstream Products

• 100665-24-5 (S)-1-{(S)-2-[(S)-3-tert-Butyldisulfanyl-2-(2-chloro-acetylamino)-propionylamino]-3-phenyl-propionyl}-pyrrolidine-2-carboxylic acid 4-nitro-phenyl ester 
• 100665-24-5 N-chloroacetyl-S-t-butylthio-L-cysteinyl-L-phenylalanyl-L-proline p-nitrophenyl ester 
• 118903-76-7 (S)-1-{(R)-2-[(R)-3-tert-Butyldisulfanyl-2-(2-chloro-acetylamino)-propionylamino]-3-phenyl-propionyl}-pyrrolidine-2-carboxylic acid 
• 118903-76-7 (S)-1-{(S)-2-[(S)-3-tert-Butyldisulfanyl-2-(2-chloro-acetylamino)-propionylamino]-3-phenyl-propionyl}-pyrrolidine-2-carboxylic acid 

Relevant articles and documents

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.