74201-47-1

Basic information

• Product Name: (tert-butoxycarbonyl)-L-tyrosyl-L-proline
• CAS NO: 74201-47-1
• Molecular Weight: 378.425
• Mol File: 74201-47-1.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: (tert-butoxycarbonyl)-L-tyrosyl-L-proline(CAS DataBase Reference)
• NIST Chemistry Reference: (tert-butoxycarbonyl)-L-tyrosyl-L-proline(74201-47-1)
• EPA Substance Registry System: (tert-butoxycarbonyl)-L-tyrosyl-L-proline(74201-47-1)

Safety Data

• Hazardous Substances Data: 74201-47-1(Hazardous Substances Data)

Upstream product

• 3978-80-1 Boc-Tyr-OH 
• 7531-52-4 L-prolinamide 
• 71591-33-8 Boc-Tyr-azide 
• 147-85-3 L-proline 
• 23506-20-9 tert-butyl (1-hydrazinyl-3-(4-hydroxyphenyl)-1-oxopropan-2-yl)carbamate 
• 82609-80-1 methyl 1-(2-((t-butoxycarbonyl)amino)-3-(4-hydroxyphenyl)propanoyl)pyrrolidine-2-carboxylate 

Downstream Products

• 96922-11-1 Boc-Tyr-Pro-Gly-OMe 
• 158976-16-0 Boc-Tyr-Pro-Gly-NH-C₃H₇(i) 
• 158976-15-9 Boc-Tyr-Pro-Ser-NHC₃H₇(i) 
• 158976-17-1 Boc-Tyr-Pro-Ser-NHCH₂C₆H₅ 
• 852333-10-9 Boc-Tyr-Pro-Ser-Ser-OMe 
• 943726-76-9 N^α-tert-butyloxycarbonyl-L-tyrosyl-L-prolyl-2'-methyl-L-phenylalanyl-L-phenylalanylamide 
• 943726-78-1 N^α-tert-butyloxycarbonyl-L-tyrosyl-L-prolyl-3',5'-dimethyl-L-phenylalanyl-L-phenylalanylamide 
• 943726-81-6 N^α-tert-butyloxycarbonyl-L-tyrosyl-L-prolyl-2',6'-dimethyl-L-tyrosyl-L-phenylalanylamide 
• 943726-83-8 N^α-tert-butyloxycarbonyl-L-tyrosyl-L-prolyl-2',4',6'-trimethyl-L-phenylalanyl-L-phenylalanylamide 
• 943726-85-0 N^α-tert-butyloxycarbonyl-L-tyrosyl-L-prolyl-2'-ethyl-6'-methyl-L-phenylalanyl-L-phenylalanylamide 
• 943726-87-2 N^α-tert-butyloxycarbonyl-L-tyrosyl-L-prolyl-2'-isopropyl-6'-methyl-L-phenylalanyl-L-phenylalanylamide 
• 96922-14-4 H-Tyr-Pro-Gly-OMe 
• 96922-16-6 Boc-Asn-Ser(Bzl)-Tyr-Pro-Gly-OMe 
• 90826-15-6 Boc-Asn-Ser(Bzl)-Tyr-Pro-Gly-NHNH₂ 

Relevant articles and documents

Short Synthesis of Oxetane and Azetidine 3-Aryl-3-carboxylic Acid Derivatives by Selective Furan Oxidative Cleavage

Four-membered rings remain underexplored motifs despite offering attractive physicochemical properties for medicinal chemistry. Arylacetic acids bearing oxetanes, azetidines, and cyclobutanes are prepared in two steps: a catalytic Friedel-Crafts reaction from four-membered ring alcohol substrates, followed by mild oxidative cleavage. The suitability of the products as building blocks is reflected in their facile purification and amenability to derivatization. Examples include heteroaromatics and aryltriflates, as well as oxetane-derived profen drug analogues and a new endomorphin derivative containing an azetidine amino acid residue.

Design, synthesis, and pharmacological characterization of novel endomorphin-1 analogues as extremely potent μ-opioid agonists

Recently we reported the synthesis and structure-activity study of endomorphin-1 (EM-1) analogues containing novel, unnatural α-methylene- β-aminopropanoic acids (Map). In the present study, we describe new EM-1 analogues containing Dmt1, (R/S)-βPro2, and (ph)Map4/(2-furyl)Map4. All of the analogues showed a high affinity for the μ-opioid receptor (MOR) and increased stability in mouse brain homogenates. Of the new compounds, Dmt1-(R)-βPro 2-Trp3-(2-furyl)Map4 (analogue 12) displayed the highest affinity toward MOR, in the picomolar range (Ki μ = 3.72 pM). Forskolin-induced cAMP accumulation assays indicated that this analogue displayed an extremely high agonistic potency, in the subpicomolar range (EC50 = 0.0421 pM, Emax = 99.5%). This compound also displayed stronger in vivo antinociceptive activity after iv administration when compared to morphine in the tail-flick test, which indicates that this analogue was able to cross the blood-brain barrier.

Efficient chemo-enzymatic synthesis of endomorphin-1 using organic solvent stable proteases to green the synthesis of the peptide

Endomorphin-1 (Tyr-Pro-Trp-Phe-NH2, EM-1), an effective analgesic, was efficiently synthesized by a combination of enzymatic and chemical methods. Peptide Boc-Trp-Phe-NH2 was synthesized with a high yield of 97.1% by the solvent-stab