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

Base Information

• Chemical Name: (2R,6S)-2,6-diaminoheptanedioic acid
• CAS No.: 922-54-3
• Molecular Formula: C₇H₁₄N₂O₄
• Molecular Weight: 190.199
• Hs Code.: 2922500090
• UNII: V5KRL7N7GD
• Nikkaji Number: J407.120D
• Wikipedia: Diaminopimelic_acid
• Wikidata: Q209275
• Metabolomics Workbench ID: 50520
• ChEMBL ID: CHEMBL415306
• Mol file: 922-54-3.mol

Synonyms:2,6 Diaminopimelic Acid;2,6-Diaminopimelic Acid;Acid, 2,6-Diaminopimelic;Acid, Diaminopimelic;Diaminopimelic Acid

Chemical Property of (2R,6S)-2,6-diaminoheptanedioic acid

Chemical Property:

• Melting Point: 340-342 °C (decomp)
• 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
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• XLogP3: -5.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 190.09535693
• Heavy Atom Count: 13
• Complexity: 175

Purity/Quality:

98%,99%, ^*data from raw suppliers

meso-2,6-Diaminopimelic acid ≥98% (TLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Amino Carboxylic Acids
• Canonical SMILES: C(CC(C(=O)O)N)CC(C(=O)O)N
• Isomeric SMILES: C(C[C@H](C(=O)O)N)C[C@@H](C(=O)O)N
• Uses: Meso-2,6-diaminopimelic acid may be used to study peptidoglycan structure and function within the cell walls of bacteria.

Technology Process of (2R,6S)-2,6-diaminoheptanedioic acid

There total 69 articles about (2R,6S)-2,6-diaminoheptanedioic 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: 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:

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

L-2-amino-6-ketopimelate

(3R,7S)-[1,2]Diazepane-3,7-dicarboxylic acid

Succinimide

Downstream raw materials:

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

(+/-)-trans-piperidine-2,6-dicarboxylic acid

cis-meso-piperidine-2,6-dicarboxylic acid

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

Refernces

• 1、 Collier, Philip N.,Campbell, Andrew D.,Patel, Ian,Raynham, Tony M.,Taylor, Richard J. K.. "Enantiomerically pure α-amino acid synthesis via hydroboration - Suzuki cross-coupling". . p. 1802 - 1815. Retrieved 2007/10/03.
• 2、 Wang,Xiong,Yang,Hruby. "An efficient synthesis of (2S, 6S)- and meso-diaminopimelic acids via asymmetric hydrogenation". . p. 94 - 98. Retrieved 2007/10/03.