952227-89-3

Basic information

• Product Name: C₄₀H₄₇N₇O₁₀
• CAS NO: 952227-89-3
• Molecular Weight: 785.854
• Mol File: 952227-89-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: C₄₀H₄₇N₇O₁₀(CAS DataBase Reference)
• NIST Chemistry Reference: C₄₀H₄₇N₇O₁₀(952227-89-3)
• EPA Substance Registry System: C₄₀H₄₇N₇O₁₀(952227-89-3)

Safety Data

• Hazardous Substances Data: 952227-89-3(Hazardous Substances Data)

Upstream product

• 71989-31-6 Fmoc-Pro-OH 
• 71989-38-3 Fmoc-Tyr(tBu)-OH 
• 143824-78-6 3-[(S)-2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)ethyl]indole-1-carboxylic acid tert-butyl ester 
• 185114-52-7 1-deoxy-1-azido-2,3,4-tri-O-acetyl-β-D-glucopyranosiduronic acid 

Relevant articles and documents

Synthesis and in vitro evaluation of a library of modified endomorphin 1 peptides

Endomorphin 1 (Endo-1 = Tyr-Pro-Trp-Phe-NH2), an endogenous opioid with high affinity and selectivity for μ-opioid receptors, mediates acute and neuropathic pain in rodents. To overcome metabolic instability and poor membrane permeability, the N- and C-termini of Endo-1 were modified by lipoamino acids (Laa) and/or sugars, and 2′,6′-dimethyltyrosine (Dmt) replacement of Tyr. Analogues were assessed for μ-opioid receptor affinity, inhibition of cAMP accumulation, enzymatic stability, and permeability across Caco-2 cell monolayers. C-Terminus modification decreased receptor affinity, while N-terminus C8-Laa improved stability and permeability with slight change in receptor affinity. Dmt provided a promising lead compound: [C8Laa-Dmt[1]]-Endo-1 is nine times more stable (t1/2 = 43.5 min), >8-fold more permeable in Caco-2 cell monolayers, and exhibits 140-fold greater μ-opioid receptor affinity (Kiμ = 0.08 nM).