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

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
The Structure and Function of the Membranes and Surfaces of Cells, 22, 77-77 (1963)
Construction and Analysis of Two Genome-Scale Deletion Libraries for Bacillus subtilis
Byoung-MoKoo
Cell Systems, 4, 291-305 (2017)
Determination of 2, 6-diaminopimelic acid in bacteria, ruminal and duodenal digesta using HPLC with fluorescence or UV detection
Czauderna M and Kowalczyk J
Journal of Animal and feed sciences, 8(5), 273-288 (1999)
Sarah N Buss et al.
International journal of systematic and evolutionary microbiology, 63(Pt 11), 4087-4093 (2013-06-04)
A Gram-staining-positive, endospore-forming rod was isolated independently from clinical specimens in New York State, USA, once in 2009 and twice in 2011. The three isolates had identical 16S rRNA gene sequences and, based on their 16S rRNA gene sequence, are...
Lilian Hor et al.
Biochimie, 95(10), 1949-1953 (2013-07-11)
DAP epimerase is the penultimate enzyme in the lysine biosynthesis pathway. The most versatile assay for DAP epimerase catalytic activity employs a coupled DAP epimerase-DAP dehydrogenase enzyme system with a commercial mixture of DAP isomers as substrate. DAP dehydrogenase converts...

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