198628-73-8

Basic information

• Product Name: (S)-2-{(S)-2-[(S)-2-Acetylamino-3-(4-benzyloxy-phenyl)-propionylamino]-3-methyl-butyrylamino}-propionic acid
• Synonyms: (S)-2-{(S)-2-[(S)-2-Acetylamino-3-(4-benzyloxy-phenyl)-propionylamino]-3-methyl-butyrylamino}-propionic acid
• CAS NO: 198628-73-8
• Molecular Weight: 483.565
• Mol File: 198628-73-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (S)-2-{(S)-2-[(S)-2-Acetylamino-3-(4-benzyloxy-phenyl)-propionylamino]-3-methyl-butyrylamino}-propionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-{(S)-2-[(S)-2-Acetylamino-3-(4-benzyloxy-phenyl)-propionylamino]-3-methyl-butyrylamino}-propionic acid(198628-73-8)
• EPA Substance Registry System: (S)-2-{(S)-2-[(S)-2-Acetylamino-3-(4-benzyloxy-phenyl)-propionylamino]-3-methyl-butyrylamino}-propionic acid(198628-73-8)

Safety Data

• Hazardous Substances Data: 198628-73-8(Hazardous Substances Data)

Upstream product

• 68858-20-8 Fmoc-Val-OH 
• 35661-39-3 N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-alanine 
• 73535-46-3 N-ac-(O-benzyl)tyrosine 

Downstream Products

• 1026965-93-4 (S)-2-[(S)-2-Acetylamino-3-(4-hydroxy-phenyl)-propionylamino]-N-((S)-1-dihexylcarbamoyl-ethyl)-3-methyl-butyramide 
• 1026248-05-4 (S)-2-[(S)-2-Acetylamino-3-(4-hydroxy-phenyl)-propionylamino]-N-[(S)-1-(2-cyclohexyl-ethylcarbamoyl)-ethyl]-3-methyl-butyramide 
• 1026823-66-4 (S)-2-[(S)-2-Acetylamino-3-(4-hydroxy-phenyl)-propionylamino]-3-methyl-N-((S)-1-phenethylcarbamoyl-ethyl)-butyramide 
• 1026287-89-7 (S)-2-[(S)-2-Acetylamino-3-(4-hydroxy-phenyl)-propionylamino]-3-methyl-N-((S)-1-pentylcarbamoyl-ethyl)-butyramide 
• 1027895-58-4 (S)-2-[(S)-2-Acetylamino-3-(4-benzyloxy-phenyl)-propionylamino]-3-methyl-N-((S)-1-phenethylcarbamoyl-ethyl)-butyramide 

Relevant articles and documents

Design of peptidomimetics that inhibit the association of phosphatidylinositol 3-kinase with platelet-derived growth factor-β receptor and possess cellular activity

Phosphorylated tyrosine residues of growth factor receptors that associate with intracellular proteins containing src-homology 2 (SH2) domains are integral components in several signal transduction pathways related to proliferative diseases such as cancer, atherosclerosis, and restenosis. In particular, a phosphorylated pentapeptide [pTyr751-Val-Pro-Met754-Leu (pTyr = phosphotyrosine)] derived from the primary sequence of platelet- derived growth factor-β (PDGF-β) receptor blocks the association of the C- terminal SH2 domain of the p85 subunit of phosphatidylinositol 3-kinase (PI 3-kinase) to PDGF-β receptor with an IC50 of 0.445 ± 0.047 μM. Further evaluation of the structure-activity relationships for pTyr751-Val-Pro- Met-Leu resulted in the design of smaller peptidomimetics with enhanced affinity including Ac-pTyr Val-Ala-N(C6H13)2 (IC50 = 0.076 ± 0.010 μM). In addition, the phosphotyrosine residue was replaced with a difluorophosphonate derivative [4-phosphono(difluoromethyl)phenylalanine (CF2Pmp)] which has been shown to be stable to cellular phosphatases. The extracellular administration of either CF2Pmp-Val-Pro-Met-Leu or Ac-CF2Pmp- Val-Pro-Met-NH2 in a whole cell assay resulted in specific inhibition of the PDGF-stimulated association from the C-terminal SH2 domain of the p85 subunit of PI 3-kinase to the PDGF-β receptor in a dose-dependent manner. These compounds were also effective in inhibiting GLUT4 translocation, c-fos expression, and cell membrane ruffling in single-cell microinjection assay.