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D1377

Sigma-Aldrich

2,6-Diaminopimelic acid

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

Sinónimos:

2,6-Diaminoheptanedioic acid

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About This Item

Fórmula lineal:
HOOCCH(NH2)(CH2)3CH(NH2)COOH
Número de CAS:
583-93-7
Peso molecular:
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

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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
Ricardo D Righetto et al.
Nature communications, 11(1), 5101-5101 (2020-10-11)
Urease converts urea into ammonia and carbon dioxide and makes urea available as a nitrogen source for all forms of life except animals. In human bacterial pathogens, ureases also aid in the invasion of acidic environments such as the stomach
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