D1377

Sigma-Aldrich

2,6-Diaminopimelic acid

≥98% (TLC)

Synonym(s):
2,6-Diaminoheptanedioic acid
Linear Formula:
HOOCCH(NH2)(CH2)3CH(NH2)COOH
CAS Number:
Molecular Weight:
190.20
Beilstein/REAXYS Number:
1787719
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.26

Quality Level

assay

≥98% (TLC)

form

powder

application(s)

peptide synthesis: suitable
thin layer chromatography (TLC): suitable

color

white to off-white

mp

~295 °C (dec.) (lit.)

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.
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. D1377.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

hazcat

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

storage_class_code

11 - Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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)
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)
Construction and Analysis of Two Genome-Scale Deletion Libraries for Bacillus subtilis
Byoung-MoKoo
Cell Systems, 4, 291-305 (2017)

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