579490-95-2

Upstream product

• 73504-61-7 diphenylalaninamide hydrochloride 
• 65864-22-4 (S)-2-amino-3-phenylpropionamide hydrochloride 
• 67729-36-6 Boc-Phe-O-COO-isoBu 
• 88463-18-7 (S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropionamide 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 33900-18-4 Cam-3508 
• 5241-58-7 L-Phenylalanine amide 

Downstream Products

• 579490-96-3 Tyr-Pro-Phe-Phe-NH₂ 
• 579491-05-7 [(S)-2-{(S)-2-[(S)-1-((S)-1-Carbamoyl-2-phenyl-ethylcarbamoyl)-2-phenyl-ethylcarbamoyl]-pyrrolidin-1-yl}-1-(4-hydroxy-2,6-dimethyl-benzyl)-2-oxo-ethyl]-carbamic acid tert-butyl ester 
• 596792-36-8 H-Tyr(2,6-Me₂)-Pro-Phe-Phe-NH₂ 
• 845623-06-5 Boc-(2',6'-diisopropyltyrosine)-Pro-Phe-Phe-NH₂ 
• 845623-05-4 Boc-(2',6'-diethyltyrosine)-Pro-Phe-Phe-NH₂ 
• 845623-07-6 Boc-(2',3',6'-trimethyltyrosine)-Pro-Phe-Phe-NH₂ 
• 845623-03-2 Boc-(2'-ethyl-6'-methyltyrosine)-Pro-Phe-Phe-NH₂ 
• 845623-04-3 Boc-(2'-isopropyl-6'-methyltyrosine)-Pro-Phe-Phe-NH₂ 
• 845623-01-0 Boc-(2'-monomethyltyrosine)-Pro-Phe-Phe-NH₂ 

Relevant academic research and scientific papers

6-Hydroxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid mimics active conformation of tyrosine in opioid peptides

6-Hydroxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid (6Htc) has been proposed as a rigid mimic of tyrosine conformation in opioid ligand-receptor complex. The significant receptor binding to mu and delta opioid receptors of respective analogues of

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.