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33240

Sigma-Aldrich

2,6-Diaminopimelic acid

≥95.0% (NT), for peptide synthesis

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:
12352103
PubChem Substance ID:
57648750
NACRES:
NA.22

product name

2,6-Diaminopimelic acid, ≥95.0% (NT)

Quality Level

100

assay

≥95.0% (NT)

form

powder

reaction suitability

reaction type: solution phase peptide synthesis

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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Application

2,6-Diaminopimelic acid (2,6-DAP) can be used as a building block in the synthesis of tripeptides , and γ-glutamyldiaminopimelic acid derivatives.

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM0943
BCCM1792
BCCL7718
BCCK7460
BCCH0213

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A new stereocontrolled synthesis of uncommon tripeptides derived from 2, 6-diaminopimelic acid (2, 6-DAP)
Paradisi F, et al.
Tetrahedron Asymmetry, 12(23), 3319-3324 (2001)
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
Peter Kämpfer et al.
International journal of systematic and evolutionary microbiology, 64(Pt 5), 1811-1816 (2014-02-22)
A Gram-staining-positive, aerobic, non-endospore forming organism, isolated as a seed endophyte (colonizing the internal healthy tissue of plant seed) of sweet corn (Zea mays), strain CSE-5610T, was studied for its taxonomic allocation. On the basis of 16S rRNA gene sequence
Structure- activity relationships in nucleotide oligomerization domain 1 (Nod1) agonistic γ-glutamyldiaminopimelic acid derivatives
Agnihotri G, et al.
Journal of Medicinal Chemistry, 54(5), 1490-1510 (2011)
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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