74992-61-3

Basic information

• Product Name: L-Proline, 1-[N-[(phenylmethoxy)carbonyl]-L-tryptophyl]-, 4-nitrophenyl ester
• CAS NO: 74992-61-3
• Molecular Formula: C30H28N4O7
• Molecular Weight: 556.575
• Mol File: 74992-61-3.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: L-Proline, 1-[N-[(phenylmethoxy)carbonyl]-L-tryptophyl]-, 4-nitrophenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Proline, 1-[N-[(phenylmethoxy)carbonyl]-L-tryptophyl]-, 4-nitrophenyl ester(74992-61-3)
• EPA Substance Registry System: L-Proline, 1-[N-[(phenylmethoxy)carbonyl]-L-tryptophyl]-, 4-nitrophenyl ester(74992-61-3)

Safety Data

• Hazardous Substances Data: 74992-61-3(Hazardous Substances Data)

Upstream product

• 2390-84-3 L-proline p-nitrophenyl ester hydrogen bromide 
• 7432-21-5 N-carbobenzyloxy-L-tryptophane 
• 40216-93-1 L-proline p-nitrophenyl ester 
• 2279-15-4 carbobenzyloxy-L-trytophan 
• 2279-15-4 2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionic acid 
• 3304-59-4 N-benzyloxycarbonyl-L-proline p-nitrophenyl ester 

Downstream Products

• 92421-73-3 N-carbobenzyloxy-L-tryptophan-L-proline thioester with N-n-dodecyl-N,N-dimethyl-N-(β-thioethyl)ammonium chloride 

Relevant articles and documents

Origins of Micellar Diastereoselectivity

Thiol-functionalized surfactant micelles (n-C12H25N+Me2CH2CH2SH,Cl-) were used to cleave Z-Trp-Pro p-nitrophenyl dipeptide esters.Marked kinetic diastereoselectivity was observed in these reactions.For example at pH 8 and concentrations (ca.6-7)x1E-3 M, the micellar thiol cleaved the LL substrate 5-6 times more rapidly than its DL diastereomer.This kinetic diastereoselectivity was shown to develop at surfactant concentrations ca.5x1E-3 M, considerably above the cmc (ca.1x1E-3 M), i.e., at a second "critical concentration".Dynamic light-scattering measurements showed that micelles which had reacted with the LL (but not the DL) substrate underwent a marked increase in apparent hydrodynamic diameter (from ca. 15 to 26 nm) near this second critical concentration.Similar phenomena could be induced upon addition of 2x1E-5 M LL dipeptide surfactant reaction product to the thiol micelles.Micelles of n-C12H25N+Me2CH2CH2OH,Cl- or n-C12H25N+Me3,Cl- were unresponsive to such additions (light scattering).The results are discussed in terms of molecular and supramolecular interactions between surfactant and solubilizate molecules.