D-2-aminoadipic acid

Base Information

• Chemical Name: D-2-aminoadipic acid
• CAS No.: 7620-28-2
• Molecular Formula: C6H11NO4
• Molecular Weight: 161.158
• Hs Code.: 29224999
• European Community (EC) Number: 616-306-8
• DSSTox Substance ID: DTXSID90227062
• Nikkaji Number: J35.843F
• Wikidata: Q27117011
• Metabolomics Workbench ID: 55522
• ChEMBL ID: CHEMBL1169505
• Mol file: 7620-28-2.mol

Synonyms:D-2-aminoadipic acid;7620-28-2;(R)-2-Aminohexanedioic acid;(2R)-2-aminohexanedioic acid;D-a-Aminoadipic acid;alpha-Aminoadipate, D-;(R)-2-Aminoadipic acid;Hexanedioic acid, 2-amino-, (2R)-;D-alpha-aminoadipic acid;(R)-2-Amino-hexanedioic acid;CHEBI:37025;Hexanedioic acid, 2-amino-, (-)- and (+)-;2-Aminohexanedioic acid (-)- and (+)-;D-Homoglutamic acid;D-|A-Aminoadipic acid;MFCD00063118;d-2-aminoadipate;Lopac-A-7275;(R)-2-Aminohexanedioicacid;SCHEMBL2022365;CHEMBL1169505;BDBM85356;DTXSID90227062;AKOS016842486;CS-W016142;NCGC00015087-01;AC-22381;AS-14204;CAS_542-32-5;EN300-86337;A838640;Q27117011;Z1255486317;D--Aminoadipic acid;H-D-Homoglu-OH

Chemical Property of D-2-aminoadipic acid

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 208-210 °C(lit.)
• Refractive Index: -24 ° (C=1, 6mol/L HCl)
• Boiling Point: 364 °C at 760 mmHg
• PKA: 2.49±0.24(Predicted)
• Flash Point: 173.9 °C
• PSA: 100.62000
• Density: 1.333 g/cm³
• LogP: 0.35350
• Storage Temp.: Store at RT.
• XLogP3: -3.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 161.06880783
• Heavy Atom Count: 11
• Complexity: 157

Purity/Quality:

99% ^*data from raw suppliers

D-2-Aminoadipic Acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CC(C(=O)O)N)CC(=O)O
• Isomeric SMILES: C(C[C@H](C(=O)O)N)CC(=O)O
• Uses: D-2-Aminoadipic Acid is a glutamine synthetase inhibitor.

Technology Process of D-2-aminoadipic acid

There total 25 articles about D-2-aminoadipic 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: 96.0%

(R)-2-chloroacetaminohexanedioic acid (71301-34-3) → D-2-aminoadipic acid (7620-28-2)

Guidance literature:

With hydrogenchloride;

DOI:10.1016/S0040-4020(01)96782-1

Reference yield: 95.0%

(E)-(R)-5-tert-Butoxycarbonylamino-hex-2-enedioic acid → D-2-aminoadipic acid (7620-28-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1016/S0040-4020(01)90305-9

Reference yield: 83.0%

(2RS)-α-Ethyl ω-methyl 2-(N-acetylamino)pimelate (156387-02-9) → D-2-aminoadipic acid (7620-28-2) + D-alpha-Aminopimelic acid (32224-57-0,3721-85-5)

Guidance literature:

With hydrogenchloride; In diethylene glycol dimethyl ether; for 48h; Yields of byproduct given; Heating;

DOI:10.1021/jo00092a029

upstream raw materials:

(+/-)-2-chloroacetaminohexanedioic acid

(R)-(+)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)chloroacetamide

L-homoglutamic acid

(R)-2-Amino-5-cyano-pentanoic acid phenylamide; hydrochloride

Downstream raw materials:

(R)-2-Amino-hexanedioic acid 6-benzyl ester

N-benzyloxycarbonyl-(D)-α-aminoadipic acid

(R)-6-oxo-piperidine-2-carboxylic acid

γ-Glu[2-amino-1-mercapto(S-EA)-6-hexanoic acid]-OH

Refernces

• 1、 Alluri, Santosh R.,Riss, Patrick J.. "Stereospecific radiosynthesis of 3-fluoro amino acids: Access to enantiomerically pure radioligands for positron emission tomography". supporting information. p. 2219 - 2224. Retrieved 2018/04/05.
• 2、 Pham,Lubell. "A practical enantioselective synthesis of α-amino dicarboxylates. Preparation of D- and L-α-aminoadipate, α-aminopimelate, and α-aminosuberate". . p. 3676 - 3680. Retrieved 2007/10/02.