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K2755

Sigma-Aldrich

2-Keto-3-deoxyoctonate ammonium salt

≥97%

Synonym(s):

3-Deoxyoctulosonic acid, KDO

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About This Item

Linear Formula:
C8H14O8 · NH3
CAS Number:
103404-70-2
Molecular Weight:
255.22
MDL number:
MFCD00057549
UNSPSC Code:
12352100
PubChem Substance ID:
57654316
NACRES:
NA.22

Assay

≥97%

form

powder

storage temp.

−20°C

SMILES string

N.OCC(O)C1OC(O)(CC(O)C1O)C(O)=O

InChI

1S/C8H14O8.H3N/c9-2-4(11)6-5(12)3(10)1-8(15,16-6)7(13)14;/h3-6,9-12,15H,1-2H2,(H,13,14);1H3

InChI key

UDJBBKGYARWWNJ-UHFFFAOYSA-N

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Application

  • Synthesis of KDO Analogues: A significant study focused on the synthesis of analogues of 3-deoxy-D-manno-octulosonic acid (KDO), which includes compounds such as 2-Keto-3-deoxyoctonate ammonium salt. These analogues were evaluated as potential inhibitors of CMP-KDO synthetase, playing a critical role in the development of new therapeutic agents targeting bacterial infections and enhancing understanding of bacterial lipopolysaccharide synthesis (Luthman et al., 1987).

Biochem/physiol Actions

KDO is a sialic acid that is a component of bacterial lipopolysaccharides and a possible target for antibiotic development.

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Campylobacter jejuni outer membrane vesicles (OMVs) contain numerous virulence-associated proteins including the cytolethal distending toxin and three serine proteases. As C. jejuni lacks the classical virulence-associated secretion systems of other enteric pathogens that deliver effectors directly into target cells, OMVs
Suwon Kim et al.
Journal of enzyme inhibition and medicinal chemistry, 35(1), 1414-1421 (2020-06-27)
Frequent occurrences of multi-drug resistance of pathogenic Gram-negative bacteria threaten human beings. The CMP-2-keto-3-deoxy-d-manno-octulosonic acid biosynthesis pathway is one of the new targets for antibiotic design. 2-Keto-3-deoxy-d-manno-octulosonate cytidylyltransferase (KdsB) is the key enzyme in this pathway. KdsB proteins from Burkholderia
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