1346799-14-1

Basic information

• Product Name: C₄₂H₅₂N₈O₁₀
• CAS NO: 1346799-14-1
• Molecular Weight: 828.922
• Mol File: 1346799-14-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: C₄₂H₅₂N₈O₁₀(CAS DataBase Reference)
• NIST Chemistry Reference: C₄₂H₅₂N₈O₁₀(1346799-14-1)
• EPA Substance Registry System: C₄₂H₅₂N₈O₁₀(1346799-14-1)

Safety Data

• Hazardous Substances Data: 1346799-14-1(Hazardous Substances Data)

Upstream product

• 15761-39-4 1-(tert-butoxycarbonyl)-L-proline 
• 3744-87-4 Boc-(R)-Ala 
• 1346799-29-8 C₁₈H₂₄N₂O₅ 
• 23680-31-1 BOC-O-benzyl-L-serine 
• 40298-71-3 N-tert-butoxycarbonyl-O-2,6-dichlorobenzyl-L-tyrosine 
• 1142953-97-6 (S)-2-amino-3-(2-cyanophenyl)-2-methylpropanoic acid hydrochloride 

Relevant articles and documents

Asymmetric synthesis and conformational analysis by NMR spectroscopy and MD of Aba- and α-MeAba-containing dermorphin analogues

Dermorphin analogues, containing a (S)- and (R)-4-amino-1,2,4,5-tetrahydro-2-benzazepin-3-one scaffold (Aba) and the α-methylated analogues as conformationally constrained phenylalanines, were prepared. Asymmetric phase-transfer catalysis was unable to provide the (S)-α-Me-o-cyanophenylalanine precursor for (S)-α-MeAba in acceptable enantiomeric purity. However, by using a Schoellkopf chiral auxiliary, this intermediate was obtained in 88% ee. [(S)-Aba3-Gly4]dermorphin retained μ-opioid affinity but displayed an increased δ-affinity. The corresponding Repimer was considerably less potent. In contrast, the [(R)-α-MeAba3-Gly4]dermorphin isomer was more potent than its Sepimer. Tar-MD simulations of both non-methylated [Aba3-Gly4]dermorphin analogues showed a degree of folding at the C-terminal residues toward the Nterminus of the peptide, without however, adopting a stabilized β-turn conformation. The α-methylated analogues, on the other hand, exhibited a typeI/I' β-turn conformation over the α-MeAba3 and Gly4 residues, which was stabilized by a hydrogen bond involving Tyr5-HN and D-Ala2-CO.