15027-03-9

Basic information

• Product Name: methyl N-[(benzyloxy)carbonyl]glycylglycylphenylalaninate
• CAS NO: 15027-03-9
• Molecular Formula: C₂₂H₂₅N₃O₆
• Molecular Weight: 427.4504
• Mol File: 15027-03-9.mol

Chemical Properties

• Boiling Point: 716.7°C at 760 mmHg
• Flash Point: 387.3°C
• Density: 1.246g/cm³
• Vapor Pressure: 2.15E-20mmHg at 25°C
• Refractive Index: 1.564
• CAS DataBase Reference: methyl N-[(benzyloxy)carbonyl]glycylglycylphenylalaninate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl N-[(benzyloxy)carbonyl]glycylglycylphenylalaninate(15027-03-9)
• EPA Substance Registry System: methyl N-[(benzyloxy)carbonyl]glycylglycylphenylalaninate(15027-03-9)

Safety Data

• Hazardous Substances Data: 15027-03-9(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 13171-93-2 N-benzyloxycarbonyl-L-glycyl-L-glycyl-L-phenylalanine 
• 2566-19-0 CbzGlyGly 
• 169676-30-6 Z-Gly-Gly-L-Phe-OCH₂CF₃ 
• 252846-38-1 Z-Gly-Gly-L-Phe-OCam 
• 13437-63-3 methyl [({[(benzyloxy)carbonyl]amino}acetyl)amino]acetate 
• 501-53-1 benzyl chloroformate 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 

Downstream Products

• 84969-56-2 Z-Gly-Gly-L-Phe-L-Leu-NH₂ 
• 113266-54-9 (S)-2-[2-(2-Benzyloxycarbonylamino-thioacetylamino)-thioacetylamino]-3-phenyl-propionic acid methyl ester 
• 2566-19-0 CbzGlyGly 
• 13171-93-2 N-benzyloxycarbonyl-L-glycyl-L-glycyl-L-phenylalanine 
• 81638-88-2 amide of N-t-butyloxycarbonyl-O-benzyl-L-tyrosylglycylglycyl-L-phenylalanyl-L-leucine 
• 82948-92-3 [des-tyr¹]-leucine enkephalinamide 
• 79396-86-4 Boc-L-Tyr-Gly-Gly-L-Phe-L-Leu-NH₂ 
• 113266-55-0 (S)-2-[2-(Benzyloxycarbonylamino-methyl)-thiazol-5-ylamino]-3-phenyl-propionic acid methyl ester 
• 60254-83-3 [des-tyr¹]-leucine enkephalin 

Relevant articles and documents

Rational Design of Small Peptides for Optimal Inhibition of Cyclooxygenase-2: Development of a Highly Effective Anti-Inflammatory Agent

Among the small peptides 2-31, (H)Gly-Gly-Phe-Leu(OMe) (30) reduced prostaglandin production of COX-2 with an IC50 of 60 nM relative to 6000 nM for COX-1. The 5 mg kg-1 dose of compound 30 rescued albino mice by 80% from capsaicin-induced paw licking and recovered it by 60% from carrageenan-induced inflammation. The mode of action of compound 30 for targeting COX-2, iNOS, and VGSC was investigated by using substance P, l-arginine, and veratrine, respectively, as biomarkers. The interactions of 30 with COX-2 were supported by isothermal calorimetry experiments showing a Ka of 6.10 ± 1.10 × 104 M-1 and ΔG of -100.3 kJ mol-1 in comparison to a Ka 0.41 × 103 ± 0.09 M-1 and ΔG of -19.2 ± 0.06 kJ mol-1 for COX-1. Moreover, compound 30 did not show toxicity up to a 2000 mg kg-1 dose. Hence, we suggest peptide 30 as a highly potent and promising candidate for further development into an anti-inflammatory drug.

α-chymotrypsin-catalysed segment condensations via the kinetically controlled approach using carbamoylmethyl esters as acyl donors in organic media

The superiority of the carbamoylmethyl ester as an acyl donor for the α-chymotrypsin-catalysed segment condensations via the kinetically controlled approach is demonstrated in several model systems carried out in organic media with low water content. Furthermore, this approach is successfully applied to the construction of the Leu-enkephalin sequence via a 4 + 1 segment coupling.