579491-20-6

Basic information

• Product Name: L-Prolinamide, N-[(1,1-dimethylethoxy)carbonyl]-2,6-dimethyl-L-tyrosyl-
• CAS NO: 579491-20-6
• Molecular Formula: C21H31N3O5
• Molecular Weight: 405.494
• Mol File: 579491-20-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: L-Prolinamide, N-[(1,1-dimethylethoxy)carbonyl]-2,6-dimethyl-L-tyrosyl-(CAS DataBase Reference)
• NIST Chemistry Reference: L-Prolinamide, N-[(1,1-dimethylethoxy)carbonyl]-2,6-dimethyl-L-tyrosyl-(579491-20-6)
• EPA Substance Registry System: L-Prolinamide, N-[(1,1-dimethylethoxy)carbonyl]-2,6-dimethyl-L-tyrosyl-(579491-20-6)

Safety Data

• Hazardous Substances Data: 579491-20-6(Hazardous Substances Data)

Upstream product

• 42429-27-6 L-prolinamide hydrochloride 
• 99953-00-1 (S)-N-Boc-2,6-dimethyltyrosine 
• 80110-73-2 2,6-dimethyl-(S)-tyrosine hydrochloride 
• 24424-99-5 di-tert-butyl dicarbonate 

Relevant articles and documents

Structural studies of [2′,6′-dimethyl-L-tyrosine1]endomorphin-2 analogues: Enhanced activity and cis orientation of the Dmt-Pro amide bond

Analogues of endomorphin-2 (EM-2: Tyr-Pro-Phe-Phe-NH2) (1) were designed to examine the importance of each residue on μ-opioid receptor interaction. Replacement of Tyr1 by 2′,6′-dimethyl-L-tyrosine (Dmt) (9-12) exerted profound effects: [Dmt1]EM-2 (9) elevated μ-opioid affinity 4.6-fold (Kiμ=0.15 nM) yet selectivity fell 330-fold as δ-affinity rose (Kiδ=28.2 nM). This simultaneous increased μ- and δ-receptor bioactivities resulted in dual agonism (IC50=0.07 and 1.87 nM, respectively). While substitution of Phe4 by a phenethyl group (4) decreased μ affinity (Kiμ=13.3 nM), the same derivative containing Dmt (12) was comparable to EM-2 but also acquired weak δ antagonism (pA2=7.05). 1H NMR spectroscopy revealed a trans configuration (1:2 to 1:3, cis/trans) in the Tyr-Pro amide bond, but a cis configuration (5:3 to 13:7, cis/trans) with Dmt-Pro analogues.