92591
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:
Molecular Weight:
190.20
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.25
MDL number:
Product Name
DL-2,6-Diaminopimelic acid, ≥95% (TLC)
SMILES string
OC([C@@H](N)CCC[C@H](N)C(O)=O)=O
InChI key
GMKMEZVLHJARHF-WHFBIAKZSA-N
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
assay
≥95% (TLC)
form
powder
Quality Level
Analysis Note
diastereometric purity ≥98.0% (HPLC)
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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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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)
The DAP pathway to lysine as a target for antimicrobial agents.
R J Cox
Natural product reports, 13(1), 29-43 (1996-02-01)
Zhaoxian Xu et al.
Scientific reports, 5, 17400-17400 (2015-12-04)
Poly(L-diaminopropionic acid) (PDAP) is one of the four homopoly(amino acid)s that have been discovered in nature. However, the molecular mechanism of PDAP biosynthesis has yet to be described. In this work, the general layout of the PDAP biosynthetic pathway is
Diaminopimelate and lysine.
Patte, J. C.
Amino Acids: Biosynthesis and Genetic Regulation, 3, 213-228 (1983)
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
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