Home Other Building Blocks KETODEOXYNONULOSONIC ACID

KETODEOXYNONULOSONIC ACID

CAS No.:
153666-19-4
Catalog Number:
AG00AQDE
Molecular Formula:
C9H16O9
Molecular Weight:
268.2179
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
5mg
≥95%
1 week
United States
$104
- +
10mg
≥95%
1 week
United States
$147
- +
25mg
≥95%
1 week
United States
$269
- +
50mg
≥95%
1 week
United States
$364
- +
Product Description
Catalog Number:
AG00AQDE
Chemical Name:
KETODEOXYNONULOSONIC ACID
CAS Number:
153666-19-4
Molecular Formula:
C9H16O9
Molecular Weight:
268.2179
MDL Number:
MFCD01863086
IUPAC Name:
(4S,5R,6R)-2,4,5-trihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
InChI:
InChI=1S/C9H16O9/c10-2-4(12)6(14)7-5(13)3(11)1-9(17,18-7)8(15)16/h3-7,10-14,17H,1-2H2,(H,15,16)/t3-,4+,5+,6+,7+,9?/m0/s1
InChI Key:
CLRLHXKNIYJWAW-QBTAGHCHSA-N
SMILES:
OC[C@H]([C@H]([C@@H]1OC(O)(C[C@@H]([C@H]1O)O)C(=O)O)O)O
Properties
Complexity:
308  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
5  
Defined Bond Stereocenter Count:
0
Exact Mass:
268.079g/mol
Formal Charge:
0
Heavy Atom Count:
18  
Hydrogen Bond Acceptor Count:
9  
Hydrogen Bond Donor Count:
7  
Isotope Atom Count:
0
Molecular Weight:
268.218g/mol
Monoisotopic Mass:
268.079g/mol
Rotatable Bond Count:
4  
Topological Polar Surface Area:
168A^2
Undefined Atom Stereocenter Count:
1  
Undefined Bond Stereocenter Count:
0
XLogP3:
-3.5  
Literature
Title Journal
Sialome analysis of the cephalochordate Branchiostoma belcheri, a key organism for vertebrate evolution. Glycobiology 20120401
Practical synthesis of 2-keto-3-deoxy-D-glycero-D-galactononulosonic acid (KDN). Organic letters 20111202
Sialoside-based pattern recognitions discriminating infections from tissue injuries. Current opinion in immunology 20110201
Stereoselective synthesis of alpha-keto-deoxy-D-glycero-D-galacto-nonulosonic acid glycosides by means of the 4,5-O-carbonate protecting group. Angewandte Chemie (International ed. in English) 20100412
Human symbiont Bacteroides thetaiotaomicron synthesizes 2-keto-3-deoxy-D-glycero-D- galacto-nononic acid (KDN). Chemistry & biology 20080922
Stereocontrolled and convergent entry to CF2-sialosides: synthesis of CF2-linked ganglioside GM4. Journal of the American Chemical Society 20071219
High-affinity ligand probes of CD22 overcome the threshold set by cis ligands to allow for binding, endocytosis, and killing of B cells. Journal of immunology (Baltimore, Md. : 1950) 20060901
Introduction. Professor Yasuo Inoue: 1934-2005. Glycoconjugate journal 20060701
KDN (deaminated neuraminic acid): dreamful past and exciting future of the newest member of the sialic acid family. Glycoconjugate journal 20060701
Structure elucidation of NeuAc, NeuGc and Kdn-containing O-glycans released from Triturus alpestris oviductal mucins. Characterization of the poly LacdiNAc sequence: HSO3(4)(GalNAcbeta1-4GlcNAcbeta1-3)1-3GalNAcbeta1-4(GlcNAcbeta1-3)0-1GlcNAcbeta1-6GalNAc-ol. Glycoconjugate journal 20060701
Identification and partial characterization of soluble and membrane-bound KDN(deaminoneuraminic acid)-glycoproteins in human ovarian teratocarcinoma PA-1, and enhanced expression of free and bound KDN in cells cultured in mannose-rich media. Glycoconjugate journal 20060701
Oral ingestion of mannose alters the expression level of deaminoneuraminic acid (KDN) in mouse organs. Glycoconjugate journal 20060701
Quantification of free sialic acid in urine by HPLC-electrospray tandem mass spectrometry: a tool for the diagnosis of sialic acid storage disease. Clinical chemistry 20040201
Engineering sialic acid synthetic ability into insect cells: identifying metabolic bottlenecks and devising strategies to overcome them. Biochemistry 20031230
Diversity of the human erythrocyte membrane sialic acids in relation with blood groups. FEBS letters 20030116
A polymer with a backbone of 3-deoxy-D-glycero-D-galacto-non-2-ulopyranosonic acid, a teichuronic acid, and a beta-glucosylated ribitol teichoic acid in the cell wall of plant pathogenic Streptomyces sp. VKM Ac-2124. European journal of biochemistry 20021201
Diversity of sialic acids revealed using gas chromatography/mass spectrometry of heptafluorobutyrate derivatives. Glycobiology 20010801
Molecular cloning of a unique CMP-sialic acid synthetase that effectively utilizes both deaminoneuraminic acid (KDN) and N-acetylneuraminic acid (Neu5Ac) as substrates. Glycobiology 20010801
Formal synthesis of (+)-3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) via desymmetrization by ring-closing metathesis. Organic letters 20010125
KDN-containing glycoprotein from loach skin mucus. Advances in experimental medicine and biology 20010101
Synthesis of CMP-deaminoneuraminic acid (CMP-KDN) using the CTP:CMP-3-deoxynonulosonate cytidylyltransferase from rainbow trout testis. Identification and characterization of a CMP-KDN synthetase. The Journal of biological chemistry 19930205
A naturally occurring deaminated neuraminic acid, 3-deoxy-D-glycero-D-galacto-nonulosonic acid (KDN). Its unique occurrence at the nonreducing ends of oligosialyl chains in polysialoglycoprotein of rainbow trout eggs. The Journal of biological chemistry 19860905
Properties