2577-62-0

Basic information

• Product Name: 2,6-DIAMINOPIMELIC ACID
• Synonyms: DIAMINOPIMELIC ACID, 2,6-;DL-2,6-DIAMINOPIMELIC ACID;DL-2,6-DIAMINOHEPTANEDIOIC ACID;DL-ALPHA,EPSILON-DIAMINOPIMELIC ACID;H-(LL,DL,MESO)DAPIM-OH;H-DL-DAPM-OH;A,E-DIAMINOPIMELIC ACID;ALPHA-EPSILON-DIAMINOPIMELIC ACID
• CAS NO: 2577-62-0
• Molecular Formula: C₇H₁₄N₂O₄
• Molecular Weight: 190.2
• EINECS: 209-524-6
• Product Categories: Amino Acids
• Mol File: 2577-62-0.mol
• Article Data: 17

Chemical Properties

• Melting Point: ~295 °C (dec.)(lit.)
• Boiling Point: 426.7°Cat760mmHg
• Flash Point: 211.8°C
• Appearance: /
• Density: 1.344g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.547
• PKA: 2.20±0.24(Predicted)
• CAS DataBase Reference: 2,6-DIAMINOPIMELIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-DIAMINOPIMELIC ACID(2577-62-0)
• EPA Substance Registry System: 2,6-DIAMINOPIMELIC ACID(2577-62-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37
• WGK Germany: 3
• Hazardous Substances Data: 2577-62-0(Hazardous Substances Data)

Usage

Uses

DL-2,6-Diaminopimelic acid, a stereoisomer of meso-DAP, may be used as a reference material in assays used to identify markers of bacteria and fungi in the rumen of ruminants.

Biochem/physiol Actions

Stereoisomer of meso-DAP. meso-DAP is a biosynthetic precursor of the essential amino acid L-lysine and component of peptidoglycan in the cell wall of many bacteria. As these functions are not observed in mammalian biochemistry, alpha,alpha′-diamino diacids (DADs) are of interest as potential antibiotics with low mammalian toxicity.

InChI:InChI=1/C7H14N2O4/c8-7(9,6(12)13)4-2-1-3-5(10)11/h1-4,8-9H2,(H,10,11)(H,12,13)

Upstream product

• 412917-46-5 dimethyl (2R,6R)-2,6-bis[(tert-butoxycarbonyl)amino]heptanedioate 
• 752179-45-6 (3R,7S)-[1,2]Diazepane-3,7-dicarboxylic acid 
• 75650-93-0 L-2-amino-6-ketopimelate 
• 41980-31-8 2,6-dicyanopiperidine 
• 922-54-3 2,6-diaminopimelic acid 
• 135560-74-6 (3S,5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-(3'-butenyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one 
• 284490-23-9 3-(3-Iodo-propyl)-1,4-bis-((S)-1-phenyl-ethyl)-piperazine-2,5-dione 
• 370860-87-0 tert-butyl (4R)-4-{(4S)-4-[(tert-butoxycarbonyl)amino]-5-methoxy-5-oxopentyl}-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 
• 370860-85-8 tert-butyl (4R)-4-{(3Z)-4-[(tert-butoxycarbonyl)amino]-5-methoxy-5-oxo-3-pentenyl}-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 
• 370860-88-1 methyl (2S,6R)-2,6-bis[(tert-butoxycarbonyl)amino]-7-hydroxyheptanoate 
• 354576-20-8 (6S,2R)-2,6-bis[(tert-butoxy)carbonylamino]-6-(methoxycarbonyl)hexanoic acid 
• 284490-24-0 (1'S,1S,1R,4R)-2,5-bis-[2,5-N,N-(1'-phenethyl)]-3,6-dioxo-2,5-diazabicyclo[3,2,2]nonane 
• 102886-93-1 racem.-2,6-bis-benzyloxycarbonylamino-heptanedioic acid diamide 
• 4243-01-0 meso-2,6-Bis--pimelinsaeure 

Downstream Products

• 20714-75-4 di-Z-meso-2,2'-diaminopimelic acid 
• 75650-93-0 L-2-amino-6-ketopimelate 
• 499-82-1 (+/-)-trans-piperidine-2,6-dicarboxylic acid 
• 59234-40-1 cis-meso-piperidine-2,6-dicarboxylic acid 
• 583-93-7 (2R,6S)-2,6-diaminoheptanedioic acid 
• 583-93-7 (2R,6R)-2,6-diaminoheptanedioic acid 
• 102886-93-1 racem.-2,6-bis-benzyloxycarbonylamino-heptanedioic acid diamide 
• 98469-29-5 C₁₇H₃₀N₂O₈ 
• 42920-79-6 meso-2,6-dibenzyloxycarbonylaminopimelic acid 
• 1227363-56-5 dibenzyl 2,6-bis((tert-butoxycarbonyl)amino)heptanedioate 
• 105541-49-9 C₂₁H₂₆N₂O₄ 
• 1227363-67-8 C₃₃H₃₈N₂O₇ 
• 75650-93-0 L-α-amino-ε-ketopimelate 
• 1269619-48-8 dibenzyl 2-amino-6-((tertbutoxycarbonyl)amino)heptanedioate 

Relevant articles and documents

A simple chromatographic route for the isolation of meso diaminopimelic acid

Meso diaminopimelic acid is an important noncoded amino acid found in Gram-negative bacterial peptidoglycan. In spite of its importance, this stereoisomer is not available commercially. A simple, economical procedure was developed for the isolation of pur

An efficient synthesis of (2S, 6S)- and meso-diaminopimelic acids via asymmetric hydrogenation

An efficient synthesis of the title compounds 1 and 2 has been successfully developed. The key step is the asymmetric hydrogenation of dehydroamino acid 7 using [Rh(I)(COD)-(S,S) or - (R,R)-Et-DuPHOS)]+OTf- to produce the optically active, protected amino acid derivatives in high ee (>95%). The approach also can be used for the synthesis of other isomers and analogues.

A concise, stereoselective synthesis of meso-2,6-diaminopimelic acid (DAP)

The preparation of meso-2,6-diaminopimelic acid 1 is described. The key step in the synthesis is Suzuki coupling of the novel organoboron homoalanine equivalent 3 with methyl (2Z)-3-bromo-2-[(tert-butoxycarbonyl)amino]-2-propenoate 5.