686-43-1

Basic information

• Product Name: H-VAL-GLY-OH
• Synonyms: VAL-GLY;L-VAL-GLY;L-VALYL-L-GLYCINE;L-VALYLGLYCINE;H-VAL-GLY-OH;2-[(2-amino-3-methylbutanoyl)amino]acetic acid;2-[(2-amino-3-methyl-butanoyl)amino]acetic acid;2-[(2-azanyl-3-methyl-butanoyl)amino]ethanoic acid
• CAS NO: 686-43-1
• Molecular Formula: C₇H₁₄N₂O₃
• Molecular Weight: 174.2
• Product Categories: amino
• Mol File: 686-43-1.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 405 °C at 760 mmHg
• Flash Point: 198.8 °C
• Appearance: /
• Density: 1.168 g/cm³
• Vapor Pressure: 1.08E-07mmHg at 25°C
• Refractive Index: 1.49
• Storage Temp.: −20°C
• Solubility: Methanol (Slightly), Water (Slightly)
• PKA: pK1:3.23(+1);pK2:8.00(0) (25°C)
• CAS DataBase Reference: H-VAL-GLY-OH(CAS DataBase Reference)
• NIST Chemistry Reference: H-VAL-GLY-OH(686-43-1)
• EPA Substance Registry System: H-VAL-GLY-OH(686-43-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 686-43-1(Hazardous Substances Data)

Usage

General Description

H-Val-Gly-OH, also known as Valylglycine, is a dipeptide consisting of the amino acids valine and glycine. This chemical compound is used in various biochemistry and chemistry research studies due to its useful properties. Amino acids, like valine and glycine, are the building blocks of proteins and play crucial roles in various biological processes, including cell growth and repair. H-Val-Gly-OH is preserved as a white crystalline powder, stable under normal temperatures and pressures. It should be stored in a cool, dry place to maintain its efficacy. H-VAL-GLY-OH should be handled with proper safety measures due to its reactivity with strong oxidants.

InChI:InChI=1/C7H14N2O3/c1-4(2)6(8)7(12)9-3-5(10)11/h4,6H,3,8H2,1-2H3,(H,9,12)(H,10,11)/t6-/m0/s1

Upstream product

• 1803-57-2 N-[N-formyl-L-valyl=>glycine 
• 22221-75-6 N-(N-benzyloxycarbonyl-L-valyl)-glycine 
• 57294-39-0 Z-Val-Gly-OBzl 
• 1738-76-7 glycine benzyl ester p-toluenesulfonic acid salt 
• 54647-77-7 N-[(benzyloxy)carbonyl]-L-valine, compound with dicyclohexylamine (1:1) 
• 74939-28-9 H-Val-Gly-OBn 
• 56-40-6 L-Glycin 
• 1676-85-3 L-Valin-N-carbonsaeureanhydrid 
• 103-72-0 phenyl isothiocyanate 
• 121574-58-1 Ac-Ala-DAPA-Val-Gly-OH 
• 204919-82-4 (6S)-6-isopropyl-2-methoxy-5-oxo-3,4,5,6-tetrahydropyrazine 
• 6000-44-8 sodium glycinate 
• 26081-02-7 (S)-N-carbamoyl-valine 
• 72-18-4 L-valine 

Downstream Products

• 95753-63-2 DL-5-isopropyl-3-<4-<(2S)-Fmocamino-2-methoxycarbonylethyl>phenyl>-2-thiohydantoin 
• 56-86-0 L-glutamic acid 
• 10148-81-9 L-γ-glutamyl-L-glutamine 

Relevant articles and documents

Structure-CaSR-activity relation of kokumi γ-glutamyl peptides

Modulation of the calcium sensing receptor (CaSR) is one of the physiological activities of γ-glutamyl peptides such as glutathione (γ-glutamylcysteinylglycine). γ-Glutamyl peptides also possess a flavoring effect, i.e., sensory activity of kokumi substances, which modifies the five basic tastes when added to food. These activities have been shown to be positively correlated, suggesting that kokumi γ-glutamyl peptides are perceived through CaSRs in humans. Our research is based on the hypothesis that the discovery of highly active CaSR agonist peptides will lead to the creation of practical kokumi peptides. Through continuous study of the structure-CaSR-activity relation of a large number of γ-glutamyl peptides, we have determined that the structural requirements for intense CaSR activity of γ-glutamyl peptides are as follows: existence of an N-terminal γ-L-glutamyl residue; existence of a moderately sized, aliphatic, neutral substituent at the second residue in an L-configuration; and existence of a C-terminal carboxylic acid, preferably with the existence of glycine as the third constituent. By the sensory analysis of γ-glutamyl peptides selected by screening using the CaSR activity assay, γ-glutamylvalylglycine was found to be a potent kokumi peptide. Furthermore, norvaline-containing γ-glutamyl peptides, i.e., γ-glutamylnorvalylglycine and γ-glutamylnorvaline, possessed excellent sensory activity of kokumi substances. A novel, practical industrial synthesis of regiospecific γ-glutamyl peptides is also required for their commercialization, which was achieved through the ring opening reaction of N-α-carbobenzoxy-L-glutamic anhydride and amino acids or peptides in the presence of N-hydroxysuccinimide.

N -boc deprotection and isolation method for water-soluble zwitterionic compounds

A highly efficient TMSI-mediated deprotection and direct isolation method to obtain zwitterionic compounds from the corresponding N-Boc derivatives has been developed. This method has been demonstrated in the final deprotection/isolation of the β-lactamase inhibitor MK-7655 as a part of its manufacturing process. Further application of this process toward other zwitterionic compounds, such as dipeptides and tripeptides, has been successfully developed. Furthermore, a catalytic version of this transformation has been demonstrated in the presence of BSA or BSTFA.

Practical synthesis of Schollkopf's bis-lactim ether chiral auxiliary: (3S)-3,6-dihydro-2,5-dimethoxy-3-isopropyl-pyrazine

Practical methodology for the bis-O-methylation of (3S)-isopropyl-piperazine-2,5-dione 4 on a 45 g scale to generate Schollkopf's bis-lactim ether chiral auxiliary (3S)-3,6-dihydro-2,5-dimethoxy-3-isopropyl-pyrazine 1 has been developed. Monomethylated intermediates 5 and 6 are reported for the first time. The gelling effects of 4 in a range of common solvents are also described.