(2S,6S)-2,6-diaminoheptanedioate

Base Information

• Chemical Name: (2S,6S)-2,6-diaminoheptanedioate
• CAS No.: 14289-34-0
• Molecular Formula: C7H14N2O4
• Molecular Weight: 190.199
• Hs Code.: 2922499990
• Mol file: 14289-34-0.mol

Synonyms:L,L-Diaminopicolinate;(2S,6S)-2,6-diaminoheptanedioate;(2S,6S)-2,6-bis(azaniumyl)heptanedioate;L,L-diaminopimelate;L,L-2,6-diaminoheptanedioate;L,L-A2pm;L,L-DAP;SCHEMBL20857026;CHEBI:57609;(2S,6S)-2,6-diammonioheptanedioate;(2S,6S)-2,6-diazaniumylheptanedioate;LL-2,6-diaminopimelic acid dizwitterion;L,L-2,6-diaminopimelic acid dizwitterion;(S,S)-2,6-diaminopimelic acid dizwitterion;(2S,6S)-2,6-diaminopimelic acid dizwitterion

Chemical Property of (2S,6S)-2,6-diaminoheptanedioate

Chemical Property:

• Vapor Pressure: 1.78E-08mmHg at 25°C
• Melting Point: 309-312 °C
• Refractive Index: 1.543
• Boiling Point: 426.7 °C at 760 mmHg
• PKA: 2.20±0.24(Predicted)
• Flash Point: 211.8 °C
• PSA: 126.64000
• Density: 1.344 g/cm³
• LogP: 0.38110
• XLogP3: -4.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 190.09535693
• Heavy Atom Count: 13
• Complexity: 164

Purity/Quality:

99% ^*data from raw suppliers

LL-2,6-Diaminopimelic acid ≥95.0% (TLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C(CC(C(=O)[O-])[NH3+])CC(C(=O)[O-])[NH3+]
• Isomeric SMILES: C(C[C@@H](C(=O)[O-])[NH3+])C[C@@H](C(=O)[O-])[NH3+]

Technology Process of (2S,6S)-2,6-diaminoheptanedioate

There total 111 articles about (2S,6S)-2,6-diaminoheptanedioate 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%

dimethyl (2R,6S)-2,6-bis[(tert-butoxycarbonyl)amino]heptanedioate (354576-23-1,370860-89-2) → (2R,6S)-2,6-diaminoheptanedioic acid (583-93-7,922-54-3,2577-62-0,14289-34-0,17121-19-6,1356383-43-1)

Guidance literature:

dimethyl (2R,6S)-2,6-bis[(tert-butoxycarbonyl)amino]heptanedioate; With hydrogenchloride; at 70 ℃; for 3h;

With methyloxirane; In ethanol; at 20 ℃; for 10h; Further stages.;

DOI:10.1021/jo010865a

Reference yield: 92.0%

(3R,7S)-[1,2]Diazepane-3,7-dicarboxylic acid (752179-45-6) → (2R,6S)-2,6-diaminoheptanedioic acid (583-93-7,922-54-3,2577-62-0,14289-34-0,17121-19-6,1356383-43-1)

Guidance literature:

With hydrogenchloride; hydrogen; platinum(IV) oxide; under 3040 Torr;

DOI:10.1248/cpb.43.535

Reference yield: 70.0%

5,5'-trimethylenedihydantoin (41980-32-9) → 2,6-diaminopimelic acid (922-54-3,2577-62-0,14289-34-0,17121-19-6,583-93-7,1356383-43-1)

Guidance literature:

With hydrogen bromide; for 36h; Heating;

upstream raw materials:

5,5'-trimethylenedihydantoin

2,6-Bis<(diphenylmethylene)-amino>-2,6-dicyanoheptane

2,6-dicyanopiperidine

di-Z-meso-2,2'-diaminopimelic acid

Downstream raw materials:

N-succinyl-L,L-diaminopimelic acid

(2R,6S)-2,6-diaminoheptanedioic acid

(S,S)-2,6-diaminopimelic acid

L-2,6-dibenzyloxycarbonylaminopimelic acid

Refernces

• 1、 Wang, Qianqian,Matsuo, Yusuke,Pradipta, Ambara R.,Inohara, Naohiro,Fujimoto, Yukari,Fukase, Koichi. "Synthesis of characteristic Mycobacterium peptidoglycan (PGN) fragments utilizing with chemoenzymatic preparation of meso-diaminopimelic acid (DAP), and their modulation of innate immune responses". supporting information. p. 1013 - 1023. Retrieved 2016/01/15.
• 2、 Toth, Gabor K.,Hetenyi, Anasztazia,Ilisz, Istvan,Peter, Antal. "A simple chromatographic route for the isolation of meso diaminopimelic acid". experimental part. p. 133 - 137. Retrieved 2011/11/05.