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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/REAXYS Number:
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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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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)
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)
Asymmetric synthesis of 2, 6-diaminopimelic acids
Williams RM and Yuan C
The Journal of Organic Chemistry, 57(24), 6519-6527 (1992)
Construction and Analysis of Two Genome-Scale Deletion Libraries for Bacillus subtilis
Byoung-MoKoo
Cell Systems, 4, 291-305 (2017)
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