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D1377

Sigma-Aldrich

2,6-Diaminopimelic acid

≥98% (TLC), suitable for thin layer chromatography (TLC)

Synonym(s):

2,6-Diaminoheptanedioic acid

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About This Item

Linear Formula:
HOOCCH(NH2)(CH2)3CH(NH2)COOH
CAS Number:
583-93-7
Molecular Weight:
190.20
Beilstein:
1787719
EC Number:
209-524-6
MDL number:
MFCD00002637
UNSPSC Code:
12352209
PubChem Substance ID:
24893417
NACRES:
NA.26

product name

2,6-Diaminopimelic acid, ≥98% (TLC)

Assay

≥98% (TLC)

form

powder

technique(s)

thin layer chromatography (TLC): suitable

color

white to off-white

mp

~295 °C (dec.) (lit.)

application(s)

peptide synthesis

SMILES string

NC(CCCC(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)

InChI key

GMKMEZVLHJARHF-UHFFFAOYSA-N

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General description

2,6-Diaminopimelic acid is produced in bacteria and is a component of cell wall. It is also synthesized by higher plants.

Application

2,6-Diaminopimelic acid (DAP) has been used:
  • as a supplement in glucose minimal media for screening Bacillus subtilis(44)
  • as a component of lysogeny broth (LB) agar for screening E coli transformants(45)
  • as a standard in thin layer chromatography for the characterization of DAP isoforms from Streptomyces strains(46)

Biochem/physiol Actions

2,6-Diaminopimelic acid is essential for microbial metabolism and is a potential marker for quantification of microbial proteins. It is a sensitive and reliable marker and is majorly quantified using gradient high-performance liquid chromatography (HPLC).

Other Notes

Mixture of LL-, DD- and meso-isomers.

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Asymmetric synthesis of 2, 6-diaminopimelic acids
Williams RM and Yuan C
The Journal of Organic Chemistry, 57(24), 6519-6527 (1992)
A rapid and precise method for the analysis of underivatized amino acids
in natural samples using volatile-ion-pairing reverse-phase liquid
chromatography?electrospray ionization tandem mass spectrometry
Jack A. Hutchings
Organic Geochemistry, 115 , 46-56 (2018)
2, 6-Diaminopimelic acid (DAPA) in microbial protein quantification of heifers fed different forage sources
Couto Filho CCC, et al.
Revista Brasileira de Zootecnia, 44(5), 180-186 (2015)
The Structure and Function of the Membranes and Surfaces of Cells, 22, 77-77 (1963)
Hui-Jing Du et al.
International journal of systematic and evolutionary microbiology, 63(Pt 3), 1068-1072 (2012-06-19)
A Gram-stain-positive, rod-shaped actinobacterium, designated strain I10A-01402(T), was isolated from surface-sterilized roots of a medicinal plant, Perilla frutescens, collected in a suburb of Beijing, China. Chemotaxonomically, the strain contained ll-diaminopimelic acid as the diagnostic diamino acid and MK-8(H4) as the
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