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92591

Sigma-Aldrich

DL-2,6-Diaminopimelic acid

≥95% (TLC)

Synonym(s):

rac.-DAP, DL-α,ε-Diaminopimelic acid, DL-2,6-Diaminoheptanedioic acid

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About This Item

Empirical Formula (Hill Notation):
C7H14N2O4
CAS Number:
2577-62-0
Molecular Weight:
190.20
MDL number:
MFCD09836080
UNSPSC Code:
12352106
PubChem Substance ID:
329770145
NACRES:
NA.25

product name

DL-2,6-Diaminopimelic acid, ≥95% (TLC)

Quality Level

100

Assay

≥95% (TLC)

form

powder

SMILES string

OC([C@@H](N)CCC[C@H](N)C(O)=O)=O

InChI

1S/C7H14N2O4/c8-4(6(10)11)2-1-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)/t4-,5-/m0/s1

InChI key

GMKMEZVLHJARHF-WHFBIAKZSA-N

Application

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.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Analysis Note

diastereometric purity ≥98.0% (HPLC)

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The DAP pathway to lysine as a target for antimicrobial agents.
R J Cox
Natural product reports, 13(1), 29-43 (1996-02-01)
Yea Hwang Moon et al.
Animal science journal = Nihon chikusan Gakkaiho, 81(6), 642-647 (2010-11-27)
A comparative study among Korean native cow (Hanwoo), Holstein dairy cow, Korean native goat and crossbred sheep on the population and marker concentration of ruminal microbes, the activities of carboxymethylcellulase (CMCase), xylanase and amylase, and in situ dry matter (DM)
Yukari Fujimoto et al.
Methods in enzymology, 478, 323-342 (2010-09-08)
In this chapter, we describe synthetic studies on partial structures of lipopolysaccharide (LPS) and peptidoglycan (PGN), which work as tags for nonself recognition in innate immune system. Our previous studies demonstrated that lipid A is the endotoxic principle of LPS.
J McKerrow et al.
Letters in applied microbiology, 30(3), 178-182 (2000-04-04)
A simple and sensitive method for separating and detecting the LL, DD and meso diastereomers of the dibasic amino acid diaminopimelic acid (DAP) in the peptidoglycan of Gram-positive bacteria is described. This method is based on reverse phase HPLC separation
A Day et al.
The Biochemical journal, 161(3), 677-685 (1977-03-01)
An enzymic assay for individual isomers (meso-, LL- and DD-) of 2,6-diaminopimelate was developed. The enzyme 2,6-diaminopimelate decarboxylase specifically attacked meso-diaminopimelate and was used to measure this isomer manometrically. The meso- and LL-isomers were measured together manometrically in a coupled
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