33912-87-7

Basic information

• Product Name: Z-GLY-VAL-OH
• Synonyms: CBZ-GLY-L-VAL;Z-GLY-VAL-OH;Z-GLYCYL-L-VALINE;N-[N-[(benzyloxy)carbonyl]glycyl]-L-valine;N-CBZ-GLY-VAL;N-(Benzyloxycarbonyl)-Gly-Val-OH;N-[N-[(Phenylmethoxy)carbonyl]glycyl]-L-valine;Z-Gly-L-Val-OH
• CAS NO: 33912-87-7
• Molecular Formula: C₁₅H₂₀N₂O₅
• Molecular Weight: 308.33
• EINECS: 251-741-3
• Mol File: 33912-87-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 577°Cat760mmHg
• Flash Point: 302.8°C
• Appearance: /
• Density: 1.226g/cm³
• Vapor Pressure: 3.73E-14mmHg at 25°C
• Refractive Index: 1.538
• Storage Temp.: -15°C
• CAS DataBase Reference: Z-GLY-VAL-OH(CAS DataBase Reference)
• NIST Chemistry Reference: Z-GLY-VAL-OH(33912-87-7)
• EPA Substance Registry System: Z-GLY-VAL-OH(33912-87-7)

Safety Data

• Hazardous Substances Data: 33912-87-7(Hazardous Substances Data)

Usage

Uses

N-(Benzyloxycarbonyl)glycyl-L-valine has been used as a reactant for the preparation of retroviral protease inhibitors. N-(Benzyloxycarbonyl)glycyl-L-valine has also been used as a reactant for the synthesis of benzimidazole derivatives.

InChI:InChI=1/C15H20N2O5/c1-10(2)13(14(19)20)17-12(18)8-16-15(21)22-9-11-6-4-3-5-7-11/h3-7,10,13H,8-9H2,1-2H3,(H,16,21)(H,17,18)(H,19,20)

Upstream product

• 61058-41-1 (S)-methyl 2-(2-(benzyloxycarbonylamino)acetamido)-3-methyl butanoate 
• 72-18-4 L-valine 
• 16748-79-1 perfluorophenyl 2-(((benzyloxy)carbonyl)amino)acetate 
• 4070-48-8 L-Valine methyl ester 
• 1138-80-3 N-(Benzyloxycarbonyl)glycine 
• 501-53-1 benzyl chloroformate 
• 6306-52-1 L-valine methylester hydrochloride 

Downstream Products

• 1147123-56-5 Cbz-Gly-Val-Leu-Ala-OtBu 
• 1201179-72-7 C₂₅H₃₈N₄O₇ 
• 1201179-84-1 C₅₁H₇₀N₆O₁₂ 
• 1584664-44-7 C₄₉H₆₆N₆O₁₂ 
• 1584664-47-0 C₄₇H₇₀N₆O₁₂S 
• 1110683-21-0 (28S,29S)-arenamide A 
• 1201179-81-8 C₂₄H₃₆N₄O₇ 
• 13795-45-4 Z-Gly-Val-Val-OMe 
• 83435-47-6 ((S)-4-Isopropyl-5-oxo-4,5-dihydro-oxazol-2-ylmethyl)-carbamic acid benzyl ester 
• 112301-23-2 EtOCO-Lys(Z)-OMe 
• 112277-26-6 Z-Gly-Val-Lys(Z)-OMe 
• 62686-54-8 Z-Gly-Val-Leu-OMe 
• 119768-16-0 (S)-2-[(R)-2-(2-Benzyloxycarbonylamino-acetylamino)-3-methyl-butyrylamino]-4-methyl-pentanoic acid methyl ester 
• 13795-44-3 Z-Gly-D-Val-Val-OMe 

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.

Total synthesis of arenamide A and its diastereomer

Arenamide A and its diastereomer have been synthesized in a convergent fashion. The key steps involved in this synthesis are Sharpless asymmetric epoxidation, C-C bond formation, and macrolactamization.

Use of polymer-bound 4-dialkylaminopyridines in peptide synthesis

This work describes the use of polymer-bound 4-dialkylaminopyridines as catalyst in peptide bond formation.In comparison with their soluble analogues, such as DMAP, these less basic compounds are less favorable to formation of oxazolone intermediate, and lead to peptide bond formation in good yields, and generally very low racemization. Key words: DMAP; polymer-bound dialkylaminopyridines; peptide synthesis; racemization.