2,6-Diaminopimelic acid
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2,6-Diaminopimelic acid

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Category
DL-Amino Acids
Catalog number
BAT-007784
CAS number
583-93-7
Molecular Formula
C7H14N2O4
Molecular Weight
190.20
2,6-Diaminopimelic acid
IUPAC Name
2,6-diaminoheptanedioic acid
Synonyms
2,6-Diaminoheptanedioic acid; Heptanedioic acid, 2,6-diamino-; DIAMINOPIMELIC ACID; M-DAP; dl-2,6-Diaminoheptanedioic acid; DL-alpha,epsilon-Diaminopimelic acid; alpha,epsilon-diaminopimelic acid; (2R,6R)-2,6-diaminoheptanedioic acid; D,L-DAP; 2,5-BIS(4-NITROPHENYL)-1,3,4-OXADIAZOLE; diaminopimelic acid; H-DL-DAPM-OH; A,E-DIAMINOPIMELIC ACID; H DL DAPM OH
Related CAS
922-54-3 (Isomer) 17121-19-6 (Isomer)
Appearance
White to yellow to pale brown crystalline powder
Purity
96.5-103.5% (Assay by titration)
Density
1.344 g/cm3
Melting Point
> 300 °C (dec.)
Boiling Point
426.7 °C at 760 mmHg
Storage
Store at RT
InChI
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
Canonical SMILES
C(CC(C(=O)O)N)CC(C(=O)O)N
2. Diaminopimelic Acid Metabolism by Pseudomonadota in the Ocean
Li-Yuan Zheng, et al. Microbiol Spectr. 2022 Oct 26;10(5):e0069122. doi: 10.1128/spectrum.00691-22. Epub 2022 Aug 30.
Diaminopimelic acid (DAP) is a unique component of the cell wall of Gram-negative bacteria. It is also an important component of organic matter and is widely utilized by microbes in the world's oceans. However, neither DAP concentrations nor marine DAP-utilizing microbes have been investigated. Here, DAP concentrations in seawater were measured and the diversity of marine DAP-utilizing bacteria and the mechanisms for their DAP metabolism were investigated. Free DAP concentrations in seawater, from surface to a 5,000 m depth, were found to be between 0.61 μM and 0.96 μM in the western Pacific Ocean. DAP-utilizing bacteria from 20 families in 4 phyla were recovered from the western Pacific seawater and 14 strains were further isolated, in which Pseudomonadota bacteria were dominant. Based on genomic and transcriptomic analyses combined with gene deletion and in vitro activity detection, DAP decarboxylase (LysA), which catalyzes the decarboxylation of DAP to form lysine, was found to be a key and specific enzyme involved in DAP metabolism in the isolated Pseudomonadota strains. Interrogation of the Tara Oceans database found that most LysA-like sequences (92%) are from Pseudomonadota, which are widely distributed in multiple habitats. This study provides an insight into DAP metabolism by marine bacteria in the ocean and contributes to our understanding of the mineralization and recycling of DAP by marine bacteria. IMPORTANCE DAP is a unique component of peptidoglycan in Gram-negative bacterial cell walls. Due to the large number of marine Gram-negative bacteria, DAP is an important component of marine organic matter. However, it remains unclear how DAP is metabolized by marine microbes. This study investigated marine DAP-utilizing bacteria by cultivation and bioinformational analysis and examined the mechanism of DAP metabolism used by marine bacteria. The results demonstrate that Pseudomonadota bacteria are likely to be an important DAP-utilizing group in the ocean and that DAP decarboxylase is a key enzyme involved in DAP metabolism. This study also sheds light on the mineralization and recycling of DAP driven by bacteria.
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