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

Base Information

• Chemical Name: (2R,3S)-2-ammonio-3-methylpentanoate
• CAS No.: 1509-35-9
• Molecular Formula: C6H13NO2
• Molecular Weight: 131.175
• Hs Code.: 29224999
• Mol file: 1509-35-9.mol

Synonyms:D-alloisoleucine zwitterion;CHEBI:85306;(2R,3S)-2-ammonio-3-methylpentanoate;(2R,3S)-2-azaniumyl-3-methyl-pentanoate;A809092

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

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 0.0309mmHg at 25°C
• Melting Point: 291 °C (dec.)(lit.)
• Refractive Index: -37 ° (C=4, 6mol/L HCl)
• Boiling Point: 225.8 °C at 760 mmHg
• PKA: 2.57±0.24(Predicted)
• Flash Point: 90.3 °C
• PSA: 63.32000
• Density: 1.035 g/cm³
• LogP: 1.14470
• Storage Temp.: 2-8°C
• Solubility.: 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:

99% ^*data from raw suppliers

D-Allo-isoleucine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36-26

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: D-allo-Isoleucine is used in the synthesis of a conjugate of epi-jasmonic acid and various antimicrobial peptides.

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

There total 147 articles about (2R,3S)-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:

maedamide → (S)-2-Hydroxy-3-methylbutanoic acid (17407-55-5) + D-alloisoleucine (1509-35-9,959215-79-3,18875-42-8) + N-methyl-D-phenylalanine (56564-52-4) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7)

Guidance literature:

With hydrogenchloride; In water; at 110 ℃; for 25h;

DOI:10.1016/j.tetlet.2014.05.099

upstream raw materials:

D-Isoleucine

D,L-β-methylenenorvaline

2-Azido-3-methyl-pentanoic acid

2-oxo-3(RS)-methylvaleric acid

Downstream raw materials:

DL-isoleucine methyl ester

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

2-Methylbutyraldehyde

L-isoleucine

Refernces

• 1、 Yajima, Tatsuo,Horikawa, Takao,Takeda, Nobuhiro,Takemura, Eri,Hattori, Hiroaki,Shimazaki, Yuichi,Shiraiwa, Tadashi. "A simple preparation of d-alloisoleucine from l-isoleucine via acetylation and separation of the ammonium salts". . p. 1285 - 1287. Retrieved 2008.
• 2、 Atherton, Eric,Benoiton, N. Leo,Brown, Evelyn,Sheppard, Robert C.,Williams, Brian J.. "Racemisation of Activated, Urethane-protected Amino-acids by p-Dimethylaminopyridine. Significance in Solid-phase Peptide Synthesis". . p. 336 - 337. Retrieved 1981.
• 3、 Diao, Shiqing,Jiang, Shuiqin,Liu, Yan,Sun, Yangyang,Wang, Hualei,Wang, Liuzhu,Wei, Dongzhi. "Rational engineering ofAcinetobacter tandoiiglutamate dehydrogenase for asymmetric synthesis ofl-homoalanine through biocatalytic cascades". . p. 4208 - 4215. Retrieved 2021/06/30.
• 4、 Cai, Weijing,Matthew, Susan,Chen, Qi-Yin,Paul, Valerie J.,Luesch, Hendrik. "Discovery of new A- and B-type laxaphycins with synergistic anticancer activity". . p. 2310 - 2319. Retrieved 2018/04/02.