{[(2S)-2-azaniumyl-3-methylbutanoyl]amino}acetate

Base Information

• Chemical Name: {[(2S)-2-azaniumyl-3-methylbutanoyl]amino}acetate
• CAS No.: 686-43-1
• Molecular Formula: C7H14 N2 O3
• Molecular Weight: 174.2
• Hs Code.: 2924199090
• Mol file: 686-43-1.mol

Synonyms:V-G zwitterion;Val-Gly zwitterion;L-Val-Gly zwitterion;valylglycine zwitterion;L-valylglycine zwitterion;CHEBI:133616;{[(2S)-2-azaniumyl-3-methylbutanoyl]amino}acetate

Chemical Property of {[(2S)-2-azaniumyl-3-methylbutanoyl]amino}acetate

Chemical Property:

• Vapor Pressure: 1.08E-07mmHg at 25°C
• Boiling Point: 405 °C at 760 mmHg
• PKA: pK1:3.23(+1);pK2:8.00(0) (25°C)
• Flash Point: 198.8 °C
• PSA: 92.42000
• Density: 1.168 g/cm³
• LogP: 0.26170
• Storage Temp.: −20°C
• Solubility.: Methanol (Slightly), Water (Slightly)
• XLogP3: -2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 174.10044231
• Heavy Atom Count: 12
• Complexity: 174

Purity/Quality:

98%min ^*data from raw suppliers

H-Val-Gly-OH ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)C(C(=O)NCC(=O)[O-])[NH3+]
• Isomeric SMILES: CC(C)[C@@H](C(=O)NCC(=O)[O-])[NH3+]

Technology Process of {[(2S)-2-azaniumyl-3-methylbutanoyl]amino}acetate

There total 30 articles about {[(2S)-2-azaniumyl-3-methylbutanoyl]amino}acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

sodium glycinate (6000-44-8) + (S)-N-carbamoyl-valine (26081-02-7) → valylglycine (686-43-1,6491-60-7)

Guidance literature:

(S)-N-carbamoyl-valine; With NO_x; oxygen; In water; at 20 ℃; under 760.051 Torr;

sodium glycinate; With sodium carbonate; In sodium hydroxide; acetonitrile; at -10 ℃; for 2h; Further stages.;

DOI:10.1002/1099-0690(200203)2002:6<1026::AID-EJOC1026>3.0.CO;2-C

Reference yield: 69.0%

tetrabutylphosphonium glycinate + L-valine methylester hydrochloride (6306-52-1) → valylglycine (686-43-1,6491-60-7)

Guidance literature:

tetrabutylphosphonium glycinate; L-valine methylester hydrochloride; at 60 ℃; for 6h; Inert atmosphere;

With acetic acid; In chloroform; at 20 ℃; for 3h;

DOI:10.1002/chem.201501783

Reference yield: 57.4%

L-Glycin (56-40-6,18875-39-3,25718-94-9) + L-Valin-N-carbonsaeureanhydrid (1676-85-3,2816-12-8,24601-74-9,43089-05-0) → L-valine (72-18-4,25609-85-2,7004-03-7,921-10-8) + valylglycine (686-43-1,6491-60-7) + Val-Val (3918-94-3) + N-carbamoylglycine (462-60-2)

Guidance literature:

With water; potassium hydroxide; potassium borate buffer; at 3 ℃; Product distribution; effect of use of various amino acid and NCA with various concentrations; effect of use various temp.; extent of hydrolysis;

upstream raw materials:

N-[N-formyl-L-valyl=>glycine

N-(N-benzyloxycarbonyl-L-valyl)-glycine

Z-Val-Gly-OBzl

glycine benzyl ester p-toluenesulfonic acid salt

Downstream raw materials:

DL-5-isopropyl-3-<4-<(2S)-Fmocamino-2-methoxycarbonylethyl>phenyl>-2-thiohydantoin

L-glutamic acid

L-γ-glutamyl-L-glutamine

Refernces

• 1、 Furukawa, Shinya,Fukuyama, Takahide,Matsui, Akihiro,Kuratsu, Mai,Nakaya, Ryotaro,Ineyama, Takashi,Ueda, Hiroshi,Ryu, Ilhyong. "Coupling-Reagent-Free Synthesis of Dipeptides and Tripeptides Using Amino Acid Ionic Liquids". supporting information. p. 11980 - 11983. Retrieved 2015/08/18.
• 2、 Lagrille, Olivier,Taillades, Jacques,Boiteau, Laurent,Commeyras, Auguste. "N-carbamoyl derivatives and their nitrosation by gaseous NOx - A new, promising tool in stepwise peptide synthesis". . p. 1026 - 1032. Retrieved 2007/10/03.