444899-84-7

Basic information

• Product Name: (2S,4S)-4-azidoproline benzyl ester
• Synonyms: (2S,4S)-4-azidoproline benzyl ester
• CAS NO: 444899-84-7
• Molecular Weight: 246.269
• Mol File: 444899-84-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (2S,4S)-4-azidoproline benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,4S)-4-azidoproline benzyl ester(444899-84-7)
• EPA Substance Registry System: (2S,4S)-4-azidoproline benzyl ester(444899-84-7)

Safety Data

• Hazardous Substances Data: 444899-84-7(Hazardous Substances Data)

Upstream product

• 89813-47-8 N-(tert-butoxycarbonyl)-(2S,4R)-4-hydroxyproline benzyl ester 
• 865295-35-8 2-benzyl 1-(tert-butyl) (2S,4R)-4-((methylsulfonyl)oxy)pyrrolidine-1,2-dicarboxylate 
• 874162-96-6 (2S,4S)-2-benzyl 1-tert-butyl 4-azidopyrrolidine-1,2-dicarboxylate 

Downstream Products

• 1018332-27-8 C₁₉H₂₈N₄O₂ 
• 1018332-26-7 C₁₉H₁₈N₄O₃ 
• 221352-74-5 (2S,4S)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-(tert-butoxycarbonylamino)pyrrolidine2-carboxylic acid 

Relevant articles and documents

Novel μ opioid antagonists derived from the μ opioid agonists endomorphin and [Dmt1]DALDA (H-Dmt-D-Arg-Phe-Lys-NH2)

Hybrid analogues of the μ opioid agonists endomorphin and [Dmt1]DALDA (H-Dmt-D-Arg-Phe-Lys-NH2, Dmt?=?2′,6′-dimethyltyrosine) containing cis-4-amino-Pro, trans-4-amino-Pro, cis-4-aminoethyl-Pro or cis-4-guanidinylethyl-Pro in the 2 p

Discovery of subnanomolar arginine-glycine-aspartate-based αvβ3/αvβ5 integrin binders embedding 4-aminoproline residues

The embodiment of 4-aminoproline residues (Amp) into the arginine-glycine-aspartate (RGD) sequence led to the discovery of a novel class of high-affinity αvβ3/αvβ 5 integrin binders [IC50h(αvβ 3) 0.03-5.12 nM; IC50h(αvβ 5) 0.88-154 nM]. A total of eight cyclopeptides of type cyclo-[-Arg-Gly-Asp-Amp-], 5-12, were assembled by a standard solid-phase peptide synthesis protocol that involved the C2-carboxyl and C4-amino functionalities of the proline scaffolds, leaving the Nα- nuclear site untouched. Functionalization of this vacant proline site with either alkyl or acyl substituents proved feasible, with significant benefit to the integrin binding capabilities of the ligands. Notably, six out of eight cyclopeptide inhibitors, 5-7 and 9-11, showed moderate yet significant selectivity toward the αvβ3 receptor. The three-dimensional structure in water was determined by NMR techniques and molecular dynamics calculations. Docking studies to the X-ray crystal structure of the extracellular segment of integrin αvβ3 complexed with reference compound 1 were also performed on selected analogues to highlight the structural features required for potent ligand binding affinity.