4-amino-2-hydroxy-2-(1H-indol-3-ylmethyl)pentanedioic Acid

Base Information

• Chemical Name: 4-amino-2-hydroxy-2-(1H-indol-3-ylmethyl)pentanedioic Acid
• CAS No.: 146142-94-1
• Molecular Formula: C14H16N2O5
• Molecular Weight: 292.291
• Metabolomics Workbench ID: 49316
• Mol file: 146142-94-1.mol

Synonyms:(2S,4S)-Monatin;4-amino-2-hydroxy-2-(1H-indol-3-ylmethyl)pentanedioic Acid;(-)-Monatin;SCHEMBL120090;SCHEMBL10088117;CHEBI:168621;RMLYXMMBIZLGAQ-UHFFFAOYSA-N;BCP28807;2-hydroxy-2-(indol-3-ylmethyl)-4aminoglutaric acid;4-hydroxy-4-(3-indolylmethyl)-2-aminoglutaric acid;(2s,4s)-2-amino-4-carboxy-4-hydroxy-5-(3-indolyl)pentanoic acid

Chemical Property of 4-amino-2-hydroxy-2-(1H-indol-3-ylmethyl)pentanedioic Acid

Chemical Property:

• Boiling Point: 656.358 °C at 760 mmHg
• Flash Point: 350.753 °C
• PSA: 136.64000
• Density: 1.526 g/cm³
• LogP: 1.02840
• XLogP3: -2.2
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 292.10592162
• Heavy Atom Count: 21
• Complexity: 416

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)CC(CC(C(=O)O)N)(C(=O)O)O
• Uses: (4S)-4-Hydroxy-4-(1H-indol-3-ylmethyl)-L-Glutamic Acid is a sweetener used in a study to analyze the anatomy of binding sites of human T1R2 and T1R3 sweet receptors.

Technology Process of 4-amino-2-hydroxy-2-(1H-indol-3-ylmethyl)pentanedioic Acid

There total 33 articles about 4-amino-2-hydroxy-2-(1H-indol-3-ylmethyl)pentanedioic Acid 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: 92.0%

(2S,4S)-4-Amino-2-(1H-indol-3-ylmethyl)-5-oxo-tetrahydro-furan-2-carboxylic acid → (2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid (146142-94-1)

Guidance literature:

With sodium hydroxide; In methanol;

DOI:10.1039/b306791m

Reference yield:

isoxazoline diethyl ester → (2R,4R)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid (400769-81-5) + (2S,4R) 4-hydroxy-4-(3-indolylmethyl)-2-aminoglutaric acid (400769-77-9) + (2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid (146142-94-1) + (2S,4R)-monatin (400769-79-1)

Guidance literature:

isoxazoline diethyl ester; With potassium hydroxide; water; sponge nickel catalyst A-7063; In ethanol; for 0.0833333h; Sealed reactor;

With hydrogen; In ethanol; water; at 20 ℃; for 1.5h; under 3750.38 Torr; Product distribution / selectivity; Sealed reactor;

Reference yield:

4-hydroxy-4-(3-indolylmethyl)-2-ketoglutaric acid (551958-84-0) → (2S,4S)-2-((1H-indol-3-yl)methyl)-4-amino-2-hydroxypentane-1,5-dioic acid (146142-94-1)

Guidance literature:

With pyridoxal 5'-phosphate; tris hydrochloride; monosodium glutamate; Aeromonas hydrophila IFO₃₈₂₀; In water; toluene; at 30 ℃; for 16h; pH=7.6; Product distribution / selectivity; Enzymatic reaction; Culture medium;

upstream raw materials:

4-amino-2-hydroxy-2-(1H-indol-3-ylmethyl)-pentanedioic acid

4-hydroxy-4-(3-indolylmethyl)-2-ketoglutaric acid

L-Tryptophan

L-alanin

Downstream raw materials:

Methyl (2S,4S)-2-(indol-3-ylmethyl)-4-(2,4-dinitroanilino)-5-oxo-2,3,4,5-tetrahydrofuran-2-carboxylate

Refernces

• 1、 -. "Polypeptides and biosynthetic pathways". Paragraph 0193. . Retrieved 2016/08/23.
• 2、 -. "Methods and systems for increasing production of equilibrium reactions". Page/Page column 19-21. . Retrieved 2010/06/20.