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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:
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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCH0213
BCCF3999
BCCC9204
BCCB6893
BCBZ7734

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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)
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)
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
Jian Zhang et al.
International journal of systematic and evolutionary microbiology, 63(Pt 5), 1776-1781 (2012-09-04)
A bacterial strain, designated D75(T), was isolated from the rhizosphere soil of Catalpa speciosa. Phylogenetic analysis based on the complete 16S rRNA gene sequence revealed that strain D75(T) was a member of the genus Paenibacillus. High levels of 16S rRNA
Soji Iida et al.
International journal of systematic and evolutionary microbiology, 55(Pt 5), 1871-1876 (2005-09-17)
The taxonomic positions of two clinically isolated actinomycetes were established using a polyphasic approach. The two strains, IFM 10032(T), isolated from ear discharge of a 28-year-old Japanese female patient with external otitis, and IFM 10148, isolated from pleural fluid of
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