Hydroxyisoleucine

Base Information

• Chemical Name: Hydroxyisoleucine
• CAS No.: 55399-93-4
• Molecular Formula: C6H13NO3
• Molecular Weight: 147.174
• Hs Code.: 1302199099
• UNII: 4SWT01T54O
• DSSTox Substance ID: DTXSID90203947
• Nikkaji Number: J1.307.775D
• Wikidata: Q27147705
• Metabolomics Workbench ID: 87113
• ChEMBL ID: CHEMBL508094
• Mol file: 55399-93-4.mol

Synonyms:(2S,3S,4R)-gamma-hydroxyisoleucine;hydroxyisoleucine

Chemical Property of Hydroxyisoleucine

Chemical Property:

• Vapor Pressure: 1.11E-05mmHg at 25°C
• Melting Point: 223-224℃
• Refractive Index: 1.495
• Boiling Point: 331.6ºCat 760 mmHg
• PKA: 2.41±0.25(Predicted)
• Flash Point: 154.4ºC
• PSA: 83.55000
• Density: 1.181 g/cm³
• LogP: 0.11550
• Storage Temp.: 2-8°C
• Solubility.: Methanol (Slightly), Water (Slightly)
• XLogP3: -2.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 147.08954328
• Heavy Atom Count: 10
• Complexity: 126

Purity/Quality:

95%-98% ^*data from raw suppliers

(4S)-4-Hydroxy-L-isoleucine ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(C)O)C(C(=O)O)N
• Isomeric SMILES: C[C@@H]([C@H](C)O)[C@@H](C(=O)O)N
• Description: 4-Hydroxyisoleucine is an amino acid that has been found in fenugreek (T. foenum graecum) seeds and has antidiabetic activity. It increases glucose-stimulated insulin release from isolated rat islets and isolated perfused rat pancreas when used at a concentration of 200 μM. In vivo, 4-hydroxyisoleucine increases PI3K activity in muscle and liver in rats when administered at a dose of 18 mg/kg and in muscle in a rat model of type 2 diabetes induced by nicotinamide and streptozotocin (STZ; ) when administered at 25 mg/kg. 4-Hydroxyisoleucine (50 mg/kg per day for four weeks) decreases plasma glucose, triglyceride, LDL, HDL, and cholesterol levels in an STZ-induced rat model of type 1 diabetes.
• Uses: (4S)-4-Hydroxy-L-isoleucine is 4S isomer of 4-Hydroxyisoleucine, which is used as a treatment for type II diabetes.

Technology Process of Hydroxyisoleucine

There total 24 articles about Hydroxyisoleucine 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: 98.0%

(3S,4R,5S)-3-amino-4,5-dimethyldihydrofuran-2(3H)-one (55527-86-1,168610-73-9,681230-42-2,695148-12-0,697797-11-8) + (3S,4R,5R)-3-Amino-4,5-dimethyl-dihydro-furan-2-one (55527-85-0,168610-73-9,681230-42-2,695148-12-0,697797-11-8) → (2S,3R,4S)-4-hydroxyisoleucine (55399-93-4,21704-86-9)

Guidance literature:

(3S,4R,5S)-3-amino-4,5-dimethyldihydrofuran-2(3H)-one; (3S,4R,5R)-3-Amino-4,5-dimethyl-dihydro-furan-2-one; With lithium hydroxide; water; at 20 ℃; for 2h;

With acetic acid;

Reference yield: 84.2%

L-isoleucine (73-32-5,959215-79-3,18875-42-8) → (2S,3R,4S)-4-hydroxyisoleucine (55399-93-4,21704-86-9)

Guidance literature:

With oxygen; α-ketoglutarate; iron(II) sulfate; sodium hydroxide; In aq. phosphate buffer; at 30 ℃; for 72h; pH=7; Temperature; pH-value; Reagent/catalyst; stereoselective reaction; Catalytic behavior; Green chemistry; Enzymatic reaction;

DOI:10.1021/acs.jafc.0c06544

Reference yield: 78.0%

(3S,4R,5S)-3-amino-4,5-dimethyl-3,4-dihydro-2(5H)-furanone hydrochloride (21704-91-6) → (2S,3R,4S)-4-hydroxyisoleucine (55399-93-4,21704-86-9)

Guidance literature:

With lithium hydroxide; In water; at 20 ℃; for 24h;

DOI:10.1002/1099-0690(200203)2002:5<834::AID-EJOC834>3.0.CO;2-6

upstream raw materials:

(3S,4R,5S)-3-amino-4,5-dimethyl-3,4-dihydro-2(5H)-furanone hydrochloride

2-Oxobutyric acid

acetaldehyde

(3SR,4RS,5SR)-3-amino-4,5-dimethyldihydrofuran-2-one

Downstream raw materials:

(2R,4S,5R,6S)-5,6-dimethyl-2-(4-nitrophenyl)-tetrahydro-2H-1,3-oxazin-4-carboxylic acid

(2R,4S,5R,6S)-5,6-dimethyl-2-phenyl-tetrahydro-2H-1,3-oxazin-4-carboxylic acid

(2R,4S,5R,6S)-2-cyclohexyl-5,6-dimethyl-tetrahydro-2H-1,3-oxazin-4-carboxylic acid

(3S,4S,5R)-3-amino-4,5-dimethyldihydrofuran-2(3H)-one

Refernces

• 1、 Davidson, Madison,McNamee, Meredith,Fan, Ruixi,Guo, Yisong,Chang, Wei-Chen. "Repurposing Nonheme Iron Hydroxylases to Enable Catalytic Nitrile Installation through an Azido Group Assistance". supporting information. p. 3419 - 3423. Retrieved 2019/03/07.
• 2、 Kumaraswamy, Gullapalli,Jayaprakash, Neerasa,Sridhar, Balasubramanian. "An organocatalyzed enantioselective synthesis of (2S,3R,4S)-4- hydroxyisoleucine and its stereoisomers". supporting information; experimental part. p. 2745 - 2747. Retrieved 2010/07/17.