3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid
(Synonyms: Deaminoneuraminic acid) 目录号 : GC42261A deaminated sialic acid
Cas No.:153666-19-4
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Sialic acids, commonly present as terminal carbohydrates on glycoconjugates, are essential for a variety of cellular functions including cell adhesion and signal recognition, as well as the formation and progression of tumors. 3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid is a deaminated sialic acid that was first identified at the nonreducing ends of oligosialyl chains in rainbow trout egg glycoprotein.[1] It is thought to be a precursor for the biosynthesis of other members of the sialic acid family.[2] 3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid can be used to analyze nonulosonic acid residues in polysialoglycoproteins.[1]
Reference:
[1]. Nadano, D., Iwasaki, M., Endo, S., et al. 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 Chemisty 261(25), 11550-11557 (1986).
[2]. Münster-Kühnel, A.K., Tiralongo, J., Krapp, S., et al. Structure and function of vertebrate CMP-sialic acid synthetases. Glycobiology 14(10), 43R-51R (2004).
| Cas No. | 153666-19-4 | SDF | |
| 别名 | Deaminoneuraminic acid | ||
| 化学名 | 3-deoxy-D-glycero-D-galacto-2-nonulopyranosonic acid | ||
| Canonical SMILES | O[C@H]1CC(C(O)=O)(O)O[C@]([C@H](O)[C@H](O)CO)([H])[C@@H]1O | ||
| 分子式 | C9H16O9 | 分子量 | 268.2 |
| 溶解度 | 30mg/mL in DMSO, 10mg/mL in DMF | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 3.7286 mL | 18.6428 mL | 37.2856 mL |
| 5 mM | 0.7457 mL | 3.7286 mL | 7.4571 mL |
| 10 mM | 0.3729 mL | 1.8643 mL | 3.7286 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
The Aspergillus fumigatus sialidase is a 3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid hydrolase (KDNase): structural and mechanistic insights
J Biol Chem 2011 Mar 25;286(12):10783-92.PMID:21247893DOI:10.1074/jbc.M110.207043.
Aspergillus fumigatus is a filamentous fungus that can cause severe respiratory disease in immunocompromised individuals. A putative sialidase from A. fumigatus was recently cloned and shown to be relatively poor in cleaving N-acetylneuraminic acid (Neu5Ac) in comparison with bacterial sialidases. Here we present the first crystal structure of a fungal sialidase. When the apo structure was compared with bacterial sialidase structures, the active site of the Aspergillus enzyme suggested that Neu5Ac would be a poor substrate because of a smaller pocket that normally accommodates the acetamido group of Neu5Ac in sialidases. A sialic acid with a hydroxyl in place of an acetamido group is 2-keto-3-deoxynononic acid (KDN). We show that KDN is the preferred substrate for the A. fumigatus sialidase and that A. fumigatus can utilize KDN as a sole carbon source. A 1.45-Å resolution crystal structure of the enzyme in complex with KDN reveals KDN in the active site in a boat conformation and nearby a second binding site occupied by KDN in a chair conformation, suggesting that polyKDN may be a natural substrate. The enzyme is not inhibited by the sialidase transition state analog 2-deoxy-2,3-dehydro-N-acetylneuraminic acid (Neu5Ac2en) but is inhibited by the related 2,3-didehydro-2,3-dideoxy-D-glycero-D-galacto-nonulosonic acid that we show bound to the enzyme in a 1.84-Å resolution crystal structure. Using a fluorinated KDN substrate, we present a 1.5-Å resolution structure of a covalently bound catalytic intermediate. The A. fumigatus sialidase is therefore a KDNase with a similar catalytic mechanism to Neu5Ac exosialidases, and this study represents the first structure of a KDNase.
Discovery of a new type of sialidase, "KDNase," which specifically hydrolyzes deaminoneuraminyl (3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid) but not N-acylneuraminyl linkages
J Biol Chem 1994 Aug 26;269(34):21415-9.PMID:8063773doi
The release of 3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid (KDN, deaminoneuraminic acid) residues from their alpha-ketosidic linkage is required to determine the structural and functional role of KDN-glycoconjugates in sources as disparate as trout egg polysialoglycoproteins and human cancers. We report for the first time the isolation and characterization of a novel type of sialidase (KDNase), which specifically hydrolyzes KDN ketosidic but not N-acylneuraminyl linkages. KDNase activity was assayed using 4-methylumbelliferyl KDN (4-MU-KDN). A KDNase-producing microorganism was identified as Sphingobacterium multivorum. The affinity-purified enzyme was designated KDNase SM to denote its origin and that it was free of N-acylneuraminidase, proteolytic, and other glycosidase activities. KDNase SM activity toward 4-MU-KDN was not inhibited by the N-acylneuraminidase inhibitor, 2,3-dehydro-2-deoxy-N-acetylneuraminic acid. KDNase SM released free KDN from naturally occurring substrates, including (KDN)GM3, KDN-glycoprotein, which bears a number of O-linked chains of KDN alpha 2-->3Gal beta 1-->3GalNAc alpha 1-->3 (KDN alpha 2-->(-->8KDN alpha 2-->)n-->6)GalNAc alpha 1-->, and the biantennary complex-type of N-glycan, KDN alpha 2-->3Gal beta 1-->4GlcNAc beta 1-->2Man alpha 1-->6(KDN alpha 2-->3Gal beta 1-->4GlcNAc beta 1-->2Man alpha 1-->3)Man beta 1-->4GlcNAc beta 1-->4GlcNAc. KDNase SM thus exhibited a broad linkage specificity and was able to hydrolyze the KDN residues ketosidically linked alpha 2-->3, alpha 2-->6, and alpha 2-->8. The enzyme did not release Neu5Ac or Neu5Gc from 4-MU-Neu5Ac, N-acetyl-neuraminyllactose, colominic acid, or other Sia(Neu5Ac or Neu5Gc)-containing glycoconjugates.
A novel sialidase capable of cleaving 3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid (KDN)
Arch Biochem Biophys 1994 Apr;310(1):243-6.PMID:8161211DOI:10.1006/abbi.1994.1163.
We have examined the tissues of several species of fish and found that the liver of the loach (Misgurnus fossilis) contains a novel sialidase capable of efficiently hydrolyzing 3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid (KDN) from the 4-methylumbelliferyl alpha-ketoside of KDN, KDN alpha 2-->3Gal beta 1-->4GlcCer and KDN alpha 2-->6 N-acetylgalactosaminitol as well as Neu5Ac from the 4-methylumbelliferyl alpha-ketoside of Neu5Ac and GM3. The pH optimum for this enzyme was determined to be 4.6, and the Km using the 4-methylumbelliferyl alpha-ketoside of KDN and 4-methylumbelliferyl alpha-ketoside of Neu5Ac as substrates were 0.07 and 0.12 mM, respectively. The enzyme was stable in the pH range of 4 to 5 but very unstable above pH 6. This is the first report of a sialidase capable of efficiently cleaving glycosidically linked KDN.
Synthesis of the nucleoside analogues of 3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid (KDN)
Nucleic Acids Symp Ser 1991;(25):137-9.PMID:1842057doi
Several mono- and di-saccharide nucleoside analogues of 3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid (KDN, 1) were synthesized under Vorbrüggen, Williamson and Koenigs-Knorr reaction conditions. The stereochemistry at the anomeric position of these compounds were elucidated by means of NMR and acid catalyzed hydrolysis.
Characterization of a deaminated neuraminic acid-containing glycoprotein from the skin mucus of the loach, Misgurnus anguillicaudatus
J Biol Chem 1994 Dec 23;269(51):32138-43.PMID:7798209doi
Using NMR spectroscopy and mass spectrometry, the major sialic acid of the skin mucus of the loach, Misgurnus anguillicaudatus was found to be 3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid (KDN). We have subsequently devised a method to isolate a KDN-containing glycoprotein preparation from loach skin mucus. The method involves the sonication of the skin mucus with 0.05 M Tris-HCl, pH 8.0, to solubilize the glycoprotein, followed by DE52-cellulose chromatography of the extract, Nuclease P1 treatment, and Sepharose CL-4B gel filtration. The purified glycoprotein preparation was found to contain 38.5% KDN, 0.4% NeuAc, 24.6% GalNAc, 3.3% Gal, and 28.2% amino acids (w/w). The amino acid composition of this glycoprotein preparation revealed that it is unusually rich in Thr, and 6 amino acids, Thr, Ser, Glu (or Gln), Pro, Gly and Ala, account for 83% of the total amino acids. This glycoprotein is extremely poor in Cys, Met, Tyr, Phe, Arg, and Trp. Treatment of this glycoprotein with alkali resulted in the destruction of 83% of Thr suggesting that most of the sugar chains in this glycoprotein are linked through Thr. Alkaline borohydride treatment of 100 mg of the glycoprotein preparation, followed by Sephadex G-25 (superfine) gel filtration, yielded two major oligosaccharide alditols, I (15.4 mg) and II (15.6 mg). Using liquid secondary ion mass spectrometry and methylation analysis, I was identified to be KDN alpha 2-->6GalNAc-ol and II, KDN alpha 2-->6(KDN alpha 2-->3)-GalNAc-o1. KDN alpha 2-->6GalNAc is structurally similar to NeuAc alpha 2-->GalNAc found in ovine submaxillary glycoprotein while II represents a novel structure which contains two sialic acids linked to a GalNAc through both alpha 2-->3 and alpha 2-->6 linkages. This structure has never been found in mucin type glycoproteins including mammalian epithelial mucin glycoproteins. This is the first report of the presence of a mucin type glycoprotein which contains KDN instead of NeuAc or NeuGc in fish skin mucus.