(2R,3R)-2-ammonio-3-methylpentanoate

Base Information

• Chemical Name: (2R,3R)-2-ammonio-3-methylpentanoate
• CAS No.: 319-78-8
• Molecular Formula: C6H13NO2
• Molecular Weight: 131.175
• Hs Code.: 29224995
• Mol file: 319-78-8.mol

Synonyms:D-isoleucine zwitterion;CHEBI:193151;(2R,3R)-2-ammonio-3-methylpentanoate;(2R,3R)-2-azaniumyl-3-methyl-pentanoate;A821084

Chemical Property of (2R,3R)-2-ammonio-3-methylpentanoate

Chemical Property:

• Appearance/Colour: white to very slightly yellow powder
• Melting Point: 272-274 °C
• Refractive Index: -40.5 ° (C=4, 6mol/L HCl)
• Boiling Point: 297.8 °C at 760 mmHg
• PKA: 2.57±0.24(Predicted)
• Flash Point: 109.2 °C
• PSA: 63.32000
• Density: 1.035 g/cm³
• LogP: 1.14470
• Storage Temp.: Store at RT.
• Solubility.: Aqueous Acid (Slightly), Water (Slightly)
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 131.094628657
• Heavy Atom Count: 9
• Complexity: 97.7

Purity/Quality:

98%min ^*data from raw suppliers

D-Isoleucine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 40
• Safety Statements: 24/25-36-22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)C(C(=O)[O-])[NH3+]
• Isomeric SMILES: CC[C@@H](C)[C@H](C(=O)[O-])[NH3+]
• Uses: May contain up to 10% allo-isomer. D-Isoleucine is not biosynthesized in the human body and is therefore categorized as an essential amino acid that must be obtained through diet. It is also an important building block that is used in the formation of hemoglobin in humans.

Technology Process of (2R,3R)-2-ammonio-3-methylpentanoate

There total 104 articles about (2R,3R)-2-ammonio-3-methylpentanoate 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: 83.0%

2-Azido-3-methyl-pentanoic acid (116847-34-8) → isoleucine (319-78-8,443-79-8,1509-34-8,1509-35-9,3107-04-8,7004-09-3,73-32-5,959215-79-3,18875-42-8)

Guidance literature:

With hydrogen; palladium on activated charcoal;

DOI:10.1016/S0040-4039(00)77143-7

Reference yield: 48.0%

DL-α-keto-β-methyl-n-valerate → isoleucine (319-78-8,443-79-8,1509-34-8,1509-35-9,3107-04-8,7004-09-3,73-32-5,959215-79-3,18875-42-8) + L-isoleucine (73-32-5,959215-79-3,18875-42-8)

Guidance literature:

With ammonium formate; tris hydrochloride; nicotinamide adenine dinucleotide; formate dehydrogenase; phenylalanine dehydrogenase; In water; at 30 ℃; for 24h;

Reference yield:

→ L-leucine (61-90-5,21675-61-6,25248-98-0,70-45-1) + D-Isoleucine (319-78-8,959215-79-3,18875-42-8)

Guidance literature:

With sulfuric acid;

upstream raw materials:

D-Isoleucine

D,L-β-methylenenorvaline

2-Azido-3-methyl-pentanoic acid

2-oxo-3(RS)-methylvaleric acid

Downstream raw materials:

D-Isoleucine methyl ester

DL-isoleucine methyl ester

(RS)-4-((RS)-sec-butyl)-oxazolidine-2,5-dione

N,N-phthaloyl-DL-isoleucine

Refernces

• 1、 Ishida, Chiharu,Miyata, Ryo,Hasebe, Fumihito,Miyata, Azusa,Kumazawa, Shigenori,Ito, Sohei,Nakano, Shogo. "Reconstruction of Hyper-Thermostable Ancestral L-Amino Acid Oxidase to Perform Deracemization to D-Amino Acids". . p. 5228 - 5235. Retrieved 2021/11/05.
• 2、 Liao, Cangsong,Seebeck, Florian P.. "Asymmetric β-Methylation of l- and d-α-Amino Acids by a Self-Contained Enzyme Cascade". supporting information. p. 7184 - 7187. Retrieved 2020/03/17.