D1377

2,6-Diaminopimelic acid

Name: 2,6-Diaminopimelic acid
Brand: SIGMA

≥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

NACRES:

NA.26

PubChem Substance ID:

24893417

UNSPSC Code:

12352209

EC Number:

209-524-6

MDL number:

MFCD00002637

Beilstein/REAXYS Number:

1787719

Product Name

2,6-Diaminopimelic acid, ≥98% (TLC)

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

SMILES string

NC(CCCC(N)C(O)=O)C(O)=O

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

Quality Level

200

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Related Categories

Amino Acids

Amino Acids, Resins & Reagents for Peptide Synthesis

Biochemicals

Cell Culture Supplements & Reagents

Building Blocks, Resins, and Coupling Reagents for GLP-1 Synthesis

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).

General description

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

Other Notes

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

pictograms

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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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)

The Structure and Function of the Membranes and Surfaces of Cells, 22, 77-77 (1963)

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)

Effect of dietary fiber and starch on fecal composition in preschool children consuming maize, amaranth, or cassava flours.

B R Hamaker et al.

Journal of pediatric gastroenterology and nutrition, 13(1), 59-66 (1991-07-01)

Metabolic balance studies were carried out in young children fed diets based on maize, amaranth, or cassava flours and in corresponding casein controls. Dietary fiber intakes were 22.2, 20.5, and 9.0 g/day for the maize, amaranth, and cassava groups, respectively.

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