1069-33-6

Basic information

• Product Name: 2,5-Diaminohexanedioic acid
• Synonyms: 2,5-Diaminohexanedioic acid
• CAS NO: 1069-33-6
• Molecular Formula: C₆H₁₂N₂O₄
• Molecular Weight: 176.1705
• Mol File: 1069-33-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 280 °C
• Boiling Point: 416.4°Cat760mmHg
• Flash Point: 205.6°C
• Appearance: /
• Density: 1.41g/cm³
• Vapor Pressure: 4.22E-08mmHg at 25°C
• Refractive Index: 1.552
• PKA: 2.10±0.28(Predicted)
• CAS DataBase Reference: 2,5-Diaminohexanedioic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Diaminohexanedioic acid(1069-33-6)
• EPA Substance Registry System: 2,5-Diaminohexanedioic acid(1069-33-6)

Safety Data

• Hazardous Substances Data: 1069-33-6(Hazardous Substances Data)

Usage

General Description

2,5-Diaminohexanedioic acid, also known as α,?-diaminocaproic acid, is a chemical compound with the molecular formula C6H12N2O4. It is a dicarboxylic acid and contains two amino groups, making it a diamine. 2,5-Diaminohexanedioic acid is used in the production of nylon-6,6, a type of synthetic polymer that is commonly used in the production of fabrics, carpets, and other materials. It is also used as a chiral resolving agent for the separation of racemic mixtures of carboxylic acids and amines. Furthermore, it has potential medical applications as a treatment for liver disease and as a protective agent against liver injury. Additionally, it has been studied for its potential to improve glucose tolerance and insulin sensitivity in individuals with diabetes.

InChI:InChI=1/C6H12N2O4/c7-3(5(9)10)1-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)

Upstream product

• 67-56-1 methanol 
• 860738-43-8 2,5-diazido-adipic acid 
• 7732-18-5 water 
• 54221-37-3 diethyl meso-2,5-dibromoadipate 
• 7647-01-0 hydrogenchloride 
• 861611-08-7 2,5-bis-(2-carboxy-benzoylamino)-adipic acid 
• 1109-18-8 dimethyl 2,5-bis(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)hexanedioate 
• 1069-28-9 dimethyl 2,5-diaminohexanedioate dihydrochloride 

Relevant articles and documents

Biomimetic Design Results in a Potent Allosteric Inhibitor of Dihydrodipicolinate Synthase from Campylobacter jejuni

Dihydrodipicolinate synthase (DHDPS), an enzyme required for bacterial peptidoglycan biosynthesis, catalyzes the condensation of pyruvate and β-aspartate semialdehyde (ASA) to form a cyclic product which dehydrates to form dihydrodipicolinate. DHDPS has, for several years, been considered a putative target for novel antibiotics. We have designed the first potent inhibitor of this enzyme by mimicking its natural allosteric regulation by lysine, and obtained a crystal structure of the protein-inhibitor complex at 2.2 ? resolution. This novel inhibitor, which we named 'bislysine', resembles two lysine molecules linked by an ethylene bridge between the α-carbon atoms. Bislysine is a mixed partial inhibitor with respect to the first substrate, pyruvate, and a noncompetitive partial inhibitor with respect to ASA, and binds to all forms of the enzyme with a Ki near 200 nM, more than 300 times more tightly than lysine. Hill plots show that the inhibition is cooperative, indicating that the allosteric sites are not independent despite being located on opposite sides of the protein tetramer, separated by approximately 50 ?. A mutant enzyme resistant to lysine inhibition, Y110F, is strongly inhibited by this novel inhibitor, suggesting this may be a promising strategy for antibiotic development.

Lithiation of Bridgehead Position in 3,6-Bridged Piperazine-2,5-diones

2,5-Dimethyl-2,5-diazabicyclooctane-3,6-dione can be lithiated at the 1,4 (bridgehead) positions with 2 equiv. of butyllithium at -78 deg C and deuterated with D2O (D0, 11.2; D1, 56.1; D2, 30.1percent).With butyllithium and methyl iodide the 1,2,5-trimethyl and 1,2,4,5-tetramethyl derivatives are obtained.Treatment of dimethyl 2,6-diaminoheptanedioate dihydrochloride with sodium methoxide in boiling butanol gives 6,8-diazabicyclononane-7,9-dione in 62percent yield.N-Methylation of this compound yields 6,8-dimethyl-6,8-diazabicyclononane-7,9-dione which can similarly be lithiated at the 1,5 (bridgehead) positions and deuterated with D2O (D0, 5.6; D1, 70.8; D2, 23.6percent).Lithiation with butyllithium and reaction with methyl iodide, benzyl iodide or bromomethyl methyl ether gives mono- and di-alkylated products at the 1,5-position.The ability to lithiate the bridgehead positions in these compounds is attributed primarily to a combination of the inductive effect of the carbonyl group and dipole stabilization by the amide nitrogen.