23631-72-3

Basic information

• Product Name: L-Phenylalanine, N-[1-[(phenylmethoxy)carbonyl]-L-prolyl]-, methyl ester
• CAS NO: 23631-72-3
• Molecular Formula: C23H26N2O5
• Molecular Weight: 410.47
• Mol File: 23631-72-3.mol
• Article Data: 17

Chemical Properties

• CAS DataBase Reference: L-Phenylalanine, N-[1-[(phenylmethoxy)carbonyl]-L-prolyl]-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: L-Phenylalanine, N-[1-[(phenylmethoxy)carbonyl]-L-prolyl]-, methyl ester(23631-72-3)
• EPA Substance Registry System: L-Phenylalanine, N-[1-[(phenylmethoxy)carbonyl]-L-prolyl]-, methyl ester(23631-72-3)

Safety Data

• Hazardous Substances Data: 23631-72-3(Hazardous Substances Data)

Upstream product

• 63-91-2 L-phenylalanine 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 147-85-3 L-proline 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 105414-01-5 Cbz-L-Pro-OCO₂-i-Bu 
• 501-53-1 benzyl chloroformate 
• 3304-59-4 N-benzyloxycarbonyl-L-proline p-nitrophenyl ester 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 

Downstream Products

• 92278-83-6 Z-Pro-Phe-Leu-Gly-NH₂ 
• 5654-85-3 (3S,8aS)-3-benzyloctahydropyrrolo[1,2-a]pyrazine-1,4-dione 
• 13589-02-1 L-prolyl-L-phenylalanine 
• 78452-05-8 [(S)-1-((S)-3-Benzyl-1,4-dioxo-hexahydro-pyrrolo[1,2-a]pyrazine-2-carbonyl)-2-methyl-propyl]-carbamic acid tert-butyl ester 
• 78452-05-8 [(S)-1-((S)-3-Benzyl-1,4-dioxo-hexahydro-pyrrolo[1,2-a]pyrazine-2-carbonyl)-2-methyl-propyl]-carbamic acid tert-butyl ester 
• 78452-07-0 (L-Valyl)-L-phenylalanyl-L-prolin-lactam 
• 78452-07-0 (S)-2-((S)-2-Amino-3-methyl-butyryl)-3-benzyl-hexahydro-pyrrolo[1,2-a]pyrazine-1,4-dione 
• 3705-26-8 L-Phenylalanyl-L-prolin-lactam 
• 3705-26-8 L-Phenylalanyl-D-prolin-lactam 
• 50868-53-6 N-(d-Lysergyl-L-valyl)-L-phenylalanyl-D-prolin-lactam 
• 50868-53-6 (6aR,9S)-7-Methyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline-9-carboxylic acid [(S)-1-((S)-3-benzyl-1,4-dioxo-hexahydro-pyrrolo[1,2-a]pyrazine-2-carbonyl)-2-methyl-propyl]-amide 
• 50868-53-6 (6aR,9S)-7-Methyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline-9-carboxylic acid [(S)-1-((S)-3-benzyl-1,4-dioxo-hexahydro-pyrrolo[1,2-a]pyrazine-2-carbonyl)-2-methyl-propyl]-amide 
• 81531-46-6 N-(9,10-Dihydrolysergyl-O-benzyl-L-seryl)-L-phenylalanyl-L-prolin-lactam 
• 81531-44-4 (6aR,9R,10aR)-7-Methyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinoline-9-carboxylic acid [(S)-1-((S)-3-benzyl-1,4-dioxo-hexahydro-pyrrolo[1,2-a]pyrazine-2-carbonyl)-2-methyl-propyl]-amide; compound with (Z)-but-2-enedioic acid 

Relevant articles and documents

Phenysilane and Silicon Tetraacetate: Versatile Promotors for Amide Synthesis

Phenylsilane was reevaluated as a useful coupling reagent for amide synthesis. At room temperature, a wide range of amides and peptides were obtained in good to excellent yields (up to 99 %). For the first time, Weinreb amides synthesis mediated by a hydrosilane were also documented. Comparative experiments with various acetoxysilanes suggested the involvement of a phenyl-triacyloxysilane. From this mechanistic study, silicon tetraacetate was shown as an efficient amine acylating agent.

Proline dipeptides containing fluorine moieties as oganocatalysts for the asymmetric aldol reaction

A series of dipeptide analogues consisting of proline, phenylalanine and aniline- or phenol-fluorine derivatives were synthesized. Their catalytic ability was evaluated in the intermolecular asymmetric aldol reaction, both in organic and aqueous media. Aniline-fluorine derivatives proved to be superior and the best results were obtained, when 2-CF3 aniline was employed. A diverse substrate scope consisting of both aromatic and aliphatic aldehydes, as well as different ketones was demonstrated, where aromatic aldehydes afforded products in high yields (up to 100%) with excellent diastereo- (up to 95:5) and enantioselectivities (up to 97%), whereas the aliphatic aldehydes afforded also excellent selectivities, but relatively low yield. A simple addition of fluorine to a dipeptide analogue affords organocatalysts with new interesting properties that can catalyze the aldol reaction more efficiently.

Evaluation of two cyclic di-peptides as inhibitors of CCL2 induced chemotaxis

Monocyte chemoattractant protein (CCL2) plays a major role in the recruitment of monocytes during inflammation. In this study we analysed properties of synthetic CCL2 inhibitors in inhibiting CCL2 mediated monocyte migration. Using trans-endothelial chemotaxis assays compounds C1 and C5 were found to significantly reduce CCL2 mediated migration. Flow based adhesion assays showed reduction in adhesion to VCAM-1 in the presence of 10 nM CCL2 and 50 μM C5 (p 0.05). Further studies with these compounds can aid in their development as anti-inflammatory therapies. The Royal Society of Chemistry 2013.