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MilliporeSigma

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:
922-54-3
Molecular Weight:
190.20
NACRES:
NA.25
PubChem Substance ID:
329748330
UNSPSC Code:
12352106
MDL number:
MFCD09836095
Beilstein/REAXYS Number:
1726899

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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

100

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This Item
3324092591105473
meso-2,6-Diaminopimelic acid ≥98% (TLC)

Sigma-Aldrich

07036

meso-2,6-Diaminopimelic acid

2,6-Diaminopimelic acid ≥95.0% (NT)

Sigma-Aldrich

33240

2,6-Diaminopimelic acid

DL-2,6-Diaminopimelic acid ≥95% (TLC)

Sigma-Aldrich

92591

DL-2,6-Diaminopimelic acid

meso-2,3-Dibromosuccinic acid 98%

Sigma-Aldrich

105473

meso-2,3-Dibromosuccinic acid

form

powder

form

powder

form

powder

form

solid

assay

≥98% (TLC)

assay

≥95.0% (NT)

assay

≥95% (TLC)

assay

98%

color

white to faint beige

color

-

color

-

color

-

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

200

application(s)

cell analysis

application(s)

peptide synthesis

application(s)

-

application(s)

-

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.[1] Component of peptidoglycan in the cell wall of many bacteria.[2][3][4]

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCK5501
BCCD2909
BCBW3645
BCBV6661
BCBT6579

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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
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.
Diaminopimelate and lysine.
Patte, J. C.
Amino Acids: Biosynthesis and Genetic Regulation, 3, 213-228 (1983)
Chiral high-performance liquid chromatographic separation of the three stereoisomers of 2,6-diaminopimelic acid without derivatization.
Nagasawa, T., et al.
Journal of Chromatography A, 653, 336-340 (1993)
N V Potekhina et al.
European journal of biochemistry, 199(2), 313-316 (1991-07-15)
The teichoic acid from the cell wall of Actinomadura cremea INA 292 has an unusual structure, being a poly(galactosylglycerol phosphate) chain with glycerol phosphate groups. Monomeric units of 1-O, beta-D-galactopyranosylglycerol monophosphate are joined in the polymer by phosphodiester links involving
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