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

Base Information

• Chemical Name: (2S,3S)-2-ammonio-3-methylpentanoate
• CAS No.: 73-32-5
• Molecular Formula: C6H13NO2
• Molecular Weight: 131.175
• Hs Code.: 29224995
• Mol file: 73-32-5.mol

Synonyms:(2S,3S)-2-ammonio-3-methylpentanoate;(2S,3S)-2-azaniumyl-3-methylpentanoate;L-isoleucine zwitterion;3f6g;3f6h;(2S,3S)-2-azaniumyl-3-methyl-pentanoate;CHEBI:58045;A837787

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

Chemical Property:

• Appearance/Colour: White crystalline powder
• Melting Point: 288 °C (dec.)(lit.)
• Refractive Index: 40.5 ° (C=4, 6mol/L HCl)
• Boiling Point: 225.772 °C at 760 mmHg
• PKA: 2.57±0.24(Predicted)
• Flash Point: 90.344 °C
• PSA: 63.32000
• Density: 1.036 g/cm³
• LogP: 1.14470
• Water Solubility.: 41.2 g/L (50℃)
• 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

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Safety Statements: S24/25:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC(C)C(C(=O)[O-])[NH3+]
• Isomeric SMILES: CC[C@H](C)[C@@H](C(=O)[O-])[NH3+]
• Nutritional Supplement: L-Isoleucine is considered a nutritional supplement that may improve central and muscular fatigue.; It can increase the serum concentration of fatigue substances, energy metabolites, and muscle soreness substances.
• Livestock and Fish Growth: Supplementing L-isoleucine in the diet may improve the growth performance of livestock and fish, such as pigs, laying hens, and juvenile Jian carp.
• Essential Amino Acid: L-Isoleucine is an essential amino acid that cannot be synthesized by the body and must be obtained from the diet.; Benefits may include regulating blood glucose, participating in hemoglobin synthesis, and reducing post-workout fatigue.
• Role in Protein Metabolism: L-Isoleucine can regulate protein metabolism, enhance immunity, and improve animal fertility.
• Industrial Uses: L-Isoleucine is widely used in food, medicine, cosmetics, feed, and other industries, showing significant commercial value and broad developmental prospects.; Corynebacterium glutamicum is one of the major strains used for L-isoleucine production.
• Biosynthetic Pathway: The biosynthetic pathway of L-isoleucine in Corynebacterium glutamicum involves 10 reaction steps originating from L-aspartate. Key genes in this pathway, such as ilvA and ilvBN, are strictly regulated.

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

There total 315 articles about (2S,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:

pholipeptin → D-Serine (312-84-5,83245-15-2) + L-threonine (72-19-5,134357-96-3,7013-32-3,82822-12-6) + (R)-leucine (328-38-1,21675-61-6,25248-98-0,70-45-1) + L-isoleucine (73-32-5,959215-79-3,18875-42-8) + (2R)-aspartic acid (1783-96-6,25608-40-6,27881-03-4,32505-46-7,52526-39-3) + L-Aspartic acid (56-84-8,25608-40-6,27881-03-4,32505-46-7,52526-39-3)

Guidance literature:

With hydrogenchloride; at 120 ℃; for 20h; Product distribution;

DOI:10.1021/jo9603993

Reference yield:

D-glucose (50-99-7) → 2-oxo-3(RS)-methylvaleric acid (1460-34-0) + L-isoleucine (73-32-5,959215-79-3,18875-42-8) + α,β-dihydroxy-β-methylvalerate (562-43-6)

Guidance literature:

With Escherichia coli TDGA; at 37 ℃; for 28h; Title compound not separated from byproducts; Microbiological reaction;

DOI:10.1271/bbb.63.672

Reference yield:

odoamide → L-alanin (56-41-7,25191-17-7,18875-37-1) + N-methylalanine (3913-67-5) + L-isoleucine (73-32-5,959215-79-3,18875-42-8) + (2R,3S)-2-hydroxy-3-methylpentanoic acid (488-15-3,51576-04-6,59653-35-9,86540-81-0,86630-77-5,70748-47-9) + N-methyl-D-phenylalanine (56564-52-4)

Guidance literature:

With hydrogenchloride; In water; at 105 ℃; for 12h;

DOI:10.1016/j.tet.2016.07.031

upstream raw materials:

D-Isoleucine

D,L-β-methylenenorvaline

2-Azido-3-methyl-pentanoic acid

2-oxo-3(RS)-methylvaleric acid

Downstream raw materials:

2-Methylbutyraldehyde

L-isoleucine

1-chloro-2-methylbutanecarboxylic acid

isoleucine tert-butyl ester

Refernces

Dynamic resolution of N-Boc-2-lithiopiperidine

10.1039/b810988e

The research focuses on the dynamic thermodynamic resolution of N-Boc-2-lithiopiperidine using chiral ligands, with the aim of enhancing the asymmetric synthesis of 2-substituted piperidines. The study explored the use of 26 chiral diamino-alkoxide ligands to achieve selectivities of up to 85:15 for the enantiomers of the organolithium compound. Key chemicals used in the process include N-Boc-piperidine, sec-butyllithium, TMEDA (tetramethylethylenediamine), and a variety of chiral ligands. The researchers found that certain ligands, particularly those derived from isoleucine and with a branched (iPr) substituent alpha to the nitrogen atom, significantly improved selectivity.

Use of diphenyliodonium bromide in the synthesis of some N-phenyl-amino acids

10.1080/00397910903051259

The research explores the synthesis of N-phenyl methyl esters of various amino acids using diphenyliodonium bromide as a key reagent. The study focuses on the efficient and selective N-phenylation of α-amino acids, including glycine, alanine, valine, leucine, isoleucine, phenylalanine, methionine, proline, serine, threonine, tyrosine, aspartic acid, and glutamic acid. The process involves converting the amino acids into their methyl ester hydrochloride salts, followed by neutralization to obtain free amines. These amines are then subjected to N-phenylation in the presence of diphenyliodonium bromide, silver nitrate, and a catalytic amount of copper bromide. The chiral integrity of the amino acids is maintained throughout the reactions, as confirmed by the synthesis of dipeptides for each N-phenyl amino acid. The structures of the new compounds are characterized using IR, 1H, and 13C NMR spectroscopy, as well as CHN microanalysis or high-resolution mass spectrometry. The study highlights the utility of diphenyliodonium bromide in the synthesis of N-phenylated amino acids, demonstrating good to excellent yields and maintaining the chirality of the starting amino acids.

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