D-Norvaline

Base Information

• Chemical Name: D-Norvaline
• CAS No.: 2013-12-9
• Molecular Formula: C5H11NO2
• Molecular Weight: 117.148
• Hs Code.: 29224919
• European Community (EC) Number: 217-936-2
• UNII: 102E6YF9W5
• DSSTox Substance ID: DTXSID40942157
• Nikkaji Number: J9.206A
• Wikipedia: Norvaline
• Wikidata: Q27103908
• Metabolomics Workbench ID: 42486
• ChEMBL ID: CHEMBL1916081
• Mol file: 2013-12-9.mol

Synonyms:alpha-aminovaleric acid;norvaline;norvaline, (DL)-isomer

Chemical Property of D-Norvaline

Chemical Property:

• Appearance/Colour: white to off-white crystals or crystalline powder
• Vapor Pressure: 0.0366mmHg at 25°C
• Melting Point: 300 °C
• Refractive Index: -25 ° (C=10, 6mol/L HCl)
• Boiling Point: 222.9 °C at 760 mmHg
• PKA: 2.54±0.20(Predicted)
• Flash Point: 88.6 °C
• PSA: 63.32000
• Density: 1.067 g/cm³
• LogP: 0.89870
• Storage Temp.: Store at RT.
• Solubility.: Aqueous Acid (Slightly), Water (Slightly)
• Water Solubility.: SOLUBLE
• XLogP3: -2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 117.078978594
• Heavy Atom Count: 8
• Complexity: 82.5

Purity/Quality:

99% ^*data from raw suppliers

D-Norvaline 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-24/25-37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC(C(=O)O)N
• Isomeric SMILES: CCC[C@H](C(=O)O)N
• Uses: D-Norvaline is used as a catalyst in the enantioselective α-bromination of carbonyl and 1,3-dicarbonyl compounds. D-Norvaline is also incorporated into jadomycins (a group of compounds that are widely used as antibiotics), ultimately producing compounds that have potential antiproliferative/anti-cancer properties.

Technology Process of D-Norvaline

There total 54 articles about D-Norvaline 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: 76.83%

DL-α-alanyl-DL-norvaline (1116-19-4,2325-18-0,39537-36-5,61500-92-3,95191-59-6,103067-82-9) → L-alanin (56-41-7,25191-17-7,18875-37-1) + D-Alanine (338-69-2,25191-17-7,18875-37-1) + D-norvaline (2013-12-9,498-18-0) + L-Norvaline (6600-40-4,498-18-0)

Guidance literature:

With (S)-1-(N,N-dimethylaminomethyl)-2-formylcymantrene; sodium methylate; copper (I) acetate; for 1h; Ambient temperature;

DOI:10.1016/0040-4020(80)80064-0

Reference yield: 5.0%

2-oxopentanoic acid (1821-02-9) → D-norvaline (2013-12-9,498-18-0) + L-Norvaline (6600-40-4,498-18-0)

Guidance literature:

With CC₁₀H₁₄NOSCH₂CH₂CH₃N(CH₃)2 ⁽⁵⁾; zinc diacetate; In methanol; at 30 ℃; Product distribution; pH 4.00; other reagent;

DOI:10.1021/ja00317a054

Reference yield:

α-ketoglutaric acid (328-50-7) + 2-aminopentanoic acid (760-78-1,498-18-0) → D-norvaline (2013-12-9,498-18-0) + D-Glutamic acid (6893-26-1,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) + L-glutamic acid (56-86-0,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6)

Guidance literature:

With pyridoxal 5'-phosphate; ω-TA from Arthrobacter sp.; branched-chain transaminase; isopropylamine; In aq. phosphate buffer; at 37 ℃; for 20h; pH=7; stereoselective reaction; Enzymatic reaction;

DOI:10.1002/adsc.201400185

upstream raw materials:

N-formyl-D,L-norvaline

N-formyl-D-norvaline

N-acetylnorvaline

N-Chloroacetyl D-norvaline

Downstream raw materials:

(2R)-2-hydroxypentanoic acid

(R)-2-(2,2,2-trifluoroacetamido)pentanoic acid

(S)-2-((S)-2-{(R)-2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-pentanoylamino}-3-phenyl-propionylamino)-succinamide

(R)-2-(N-benzyloxycarbonylamino)pentanoic acid

Refernces

• 1、 Pereira, Pedro C.,Arends, Isabel W.C.E.,Sheldon, Roger A.. "A green and expedient synthesis of enantiopure diketopiperazines via enzymatic resolution of unnatural amino acids". . p. 4991 - 4993. Retrieved 2014.
• 2、 Zhang, Danping,Jing, Xiaoran,Zhang, Wenli,Nie, Yao,Xu, Yan. "Highly selective synthesis of d-amino acids from readily available l-amino acids by a one-pot biocatalytic stereoinversion cascade". . p. 29927 - 29935. Retrieved 2019/10/01.
• 3、 Cheng, Xinkuan,Chen, Xi,Feng, Jinhui,Wu, Qiaqing,Zhu, Dunming. "Structure-guided engineering of: Meso -diaminopimelate dehydrogenase for enantioselective reductive amination of sterically bulky 2-keto acids". . p. 4994 - 5002. Retrieved 2018/10/17.