07036
meso-2,6-Diaminopimelic acid
≥98% (TLC)
Synonym(s):
(2SR, 6RS)-2,6-Diaminoheptanedioic acid, meso-DAP
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About This Item
Empirical Formula (Hill Notation):
C7H14N2O4
CAS Number:
Molecular Weight:
190.20
NACRES:
NA.25
PubChem Substance ID:
UNSPSC Code:
12352106
MDL number:
Beilstein/REAXYS Number:
1726899
SMILES string
N[C@H](CCC[C@H](N)C(O)=O)C(O)=O, N[C@H](CCC[C@H](N)C(O)=O)C(O)=O
InChI key
GMKMEZVLHJARHF-SYDPRGILSA-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+
assay
≥98% (TLC)
form
powder
color
white to faint beige
application(s)
cell analysis
Quality Level
Related Categories
Application
Meso-2,6-diaminopimelic acid may be used to study peptidoglycan structure and function within the cell walls of bacteria.
Biochem/physiol Actions
Penultimate biosynthetic precursor of the essential amino acid L-lysine. Component of peptidoglycan in the cell wall of many bacteria.
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Luigi Franchi et al.
Cellular microbiology, 10(1), 1-8 (2007-10-20)
The innate immune system comprises several classes of pattern-recognition receptors, including Toll-like receptors (TLRs) and nucleotide binding and oligomerization domain-like receptors (NLRs). TLRs recognize microbes on the cell surface and in endosomes, whereas NLRs sense microbial molecules in the cytosol.
S Satyanarayana et al.
Amino acids, 21(3), 221-235 (2002-01-05)
Peptidoglycans isolated from two Fusobacterium species of anaerobic bacteria were analyzed for constituent amino acids. Hydrolysis conditions were varied to optimize the yield of diamino acids from peptidoglycan. The o-phthalaldehyde derivatives of the diamino acid stereoisomers were separated by high-performance
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.
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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