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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
BCCM0943
BCCM1792
BCCL7718
BCCK7460
BCCH0213

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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)
Feiyu Jia et al.
Antonie van Leeuwenhoek, 103(2), 399-408 (2012-09-27)
A novel endophytic actinomycete, designated strain NEAU-J3(T), was isolated from soybean root (Glycine max (L.) Merr) and characterized using a polyphasic approach. Phylogenetic analysis based on 16S rRNA gene sequences suggested that strain NEAU-J3(T) fell within the family Micromonosporaceae. The
Hui-Jing Du et al.
International journal of systematic and evolutionary microbiology, 63(Pt 3), 1068-1072 (2012-06-19)
A Gram-stain-positive, rod-shaped actinobacterium, designated strain I10A-01402(T), was isolated from surface-sterilized roots of a medicinal plant, Perilla frutescens, collected in a suburb of Beijing, China. Chemotaxonomically, the strain contained ll-diaminopimelic acid as the diagnostic diamino acid and MK-8(H4) as the
E Castillo-Lopez et al.
Journal of animal science, 91(2), 924-934 (2012-11-14)
The objectives of this trial were to determine the rumen undegradable protein (RUP) of dried distillers grains with solubles (DDGS), to compare the estimates of duodenal bacterial CP (BCP) flow using diaminopumelic acid (DAPA) or DNA as bacterial markers, and
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