Skip to Content
Merck
All Photos(1)

Documents

07036

Sigma-Aldrich

meso-2,6-Diaminopimelic acid

≥98% (TLC)

Synonym(s):

(2SR, 6RS)-2,6-Diaminoheptanedioic acid, meso-DAP

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C7H14N2O4
CAS Number:
922-54-3
Molecular Weight:
190.20
Beilstein:
1726899
MDL number:
MFCD09836095
UNSPSC Code:
12352106
PubChem Substance ID:
329748330
NACRES:
NA.25

Quality Level

100

Assay

≥98% (TLC)

form

powder

color

white to faint beige

application(s)

cell analysis

SMILES string

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

InChI key

GMKMEZVLHJARHF-SYDPRGILSA-N

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 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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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
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
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service