3,5-dideoxy-L-glycero-L-galacto-2-nonulosonic acid | 75003-84-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,5-dideoxy-L-glycero-L-galacto-2-nonulosonic acid
• 英文别名: 3,5-dideoxy-D-arabino-D-glycero-nonulosonic acid；3,5-dideoxy-D-gluco-2-nonulosonic acid；(2S,4R,6R)-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 75003-84-8
• 化学式: C₉H₁₆O₈
• 分子量: 252.221
• InChiKey: MTINJFBMGGVKEV-BTPGUECKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  148
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3,5-dideoxy-L-glycero-L-galacto-2-nonulosonic acid 在 氢气 作用下， 以 吡啶 为溶剂， 生成
  参考文献：
  名称：

  Chemical and enzymatic synthesis of high-affinity selectin ligands

  摘要：

  Analogs of sialyl Lewis(x) have been synthesized chemically using donors of modified sialic acids. The sialic acids were obtained enzymatically by an aldolase reaction. The sLe(x) tetrasaccharides modified at C-2 of the GlcNAc moiety and at C-5 of the sialic acid residue were tested as inhibitors for E- and P-selectins. Up to 12-fold higher inhibitory potency was found for the lyse-derivative of sLeX compared to the parent compound. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00051-6
• 作为产物：
  描述：

  2-Deoxy-D-glucose 、 sodium pyruvate 在 sodium azide 、 potassium phosphate buffer 、 acylneuraminate pyruvate lyase 、 agarose 、 1,4-二巯基-2,3-丁二醇 作用下， 生成 3,5-dideoxy-L-glycero-L-galacto-2-nonulosonic acid
  参考文献：
  名称：

  固定化醛缩酶在天然脱氨基神经氨酸的首次合成中的用途

  摘要：

  3-脱氧第一合成d -甘油基- d -半乳糖-nonulosonic酸（KDN）（1）通过非氮肥的基板的缩合来实现d -甘露糖（2）与丙酮酸，由固定化acylneuraminate丙酮酸裂解催化。

  DOI：

  10.1039/c39870000859

文献信息

• Sialyl aldolase in organic synthesis: from the trout egg acid 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) to branched-chain higher ketoses as possible new chirons.
  作者：Claudine Augé、Christine Gautheron、Serge David、Annie Malleron、Bertrand Cavayé、Bénédicte Bouxom

  DOI：10.1016/s0040-4020(01)97593-3

  日期：1990.1

  N-Acetylneuraminate pyruvate lyase accepts as substrates varied non-nitrogeneous sugars. Condensation of pyruvate with D-mannose yields 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) a component of rainbow trout egg polysialoglycoprotein. From some easily available monosaccharides were prepared other ulosonic acids: 3-deoxy-D-galacto-2-octulosonic 35dideoxy-D-gluco-2-nonulosonic and 37-dideo

  N-乙酰神经氨酸丙酮酸裂解酶接受各种非氮源糖作为底物。丙酮酸与D-甘露糖的缩合产生3-脱氧-D-甘油-D-半乳糖-2-壬基磺酸（KDN），它是虹鳟鱼卵多唾液酸糖蛋白的一种成分。从一些容易得到的单糖制备其它ulosonic酸：3-脱氧-D-半乳-2-辛酮糖35dideoxy-D-葡糖-2- nonulosonic和37二脱氧D-半乳-2- nonulosonic酸。葡萄糖不是良好的底物，D-阿拉伯糖产生了预期的3-脱氧-D-葡萄糖的混合物-2-辛基磺酸（19％）和3-脱氧-D-甘露糖-2-辛基磺酸（16％）。后者是来自细菌多糖的众所周知的糖酸KDO，其是由缩合步骤中的异常取向导致的。通过保留2-脱氧-2- C -2-苯基-D-的76％收率的转化，证明了酶对糖的C（2）处的取代基的性质的相对冷漠，只要保留了D-甘露聚糖构型即可。甘露糖转化成35-二脱氧-5 - C-苯基-D-葡萄糖-2-壬基磺
• Kuznik; Unverzagt, Carlo; Hoersch, Journal fur Praktische Chemie (Weinheim), 2000, vol. 342, # 8, p. 745 - 752
  作者：Kuznik、Unverzagt, Carlo、Hoersch、Kretzschmar

  DOI：——

  日期：——
• Unusual stereoselectivity in sialic acid aldolase-catalyzed aldol condensations: synthesis of both enantiomers of high-carbon monosaccharides
  作者：Chun Hung Lin、Takeshi Sugai、Randall L. Halcomb、Yoshitaka Ichikawa、Chi Huey Wong

  DOI：10.1021/ja00052a008

  日期：1992.12

  An inversion of stereoselectivity in aldol condensations catalyzed by sialic acid aldolase (from Escherichia coli, Shinko American Inc.) was observed when L-mannose, 6-deoxy-L-mannose, L-talose, 2-deoxy-L-glucose, 2-deoxy-L-rhamnose, N-acetyl-L-mannosamine, D-gulose, D-arabinose, and 2-azido-2-deoxy-L-mannose were used as acceptor substrates. In all substrates tested, except the last three, a complete inversion of stereoselectivity was observed; i.e., the C-nucleophile of pyruvate attacks the re face of the acceptor carbonyl instead of the si face as in the normal case for the enantiomeric substrates. Examination of the product distribution during the course of enzymatic reactions indicates that the stereoselectivity is thermodynamically controlled in nature; i.e., attack on the re face would take place if the resulting product would be more stable than the one from the si face attack. Both enantiomers of several high-carbon monosaccharides are now accessible via the aldolase reactions. A new practical procedure has also been developed for the preparation of the aldolase products where unreacted pyruvate (usually used in 7-fold excess to drive the reaction) is decomposed with pyruvate decarboxylase to simplify product isolation.
• Overproduction of CMP-sialic acid synthetase for organic synthesis
  作者：Jennifer Lin Chun Liu、Gwo Jenn Shen、Yoshitaka Ichikawa、James F. Rutan、Gerardo Zapata、Willie F. Vann、Chi Huey Wong

  DOI：10.1021/ja00036a044

  日期：1992.5

  The gene coding for Escherichia coli CMP-sialic acid synthetase (E.C. 2.7.7.43) was cloned and overexpressed in E. coli through a primer-directed polymerase chain reaction. Two plasmids were constructed to produce the native enzyme and a modified enzyme fused with a decapeptide at the C-terminus. The decapeptide tag was used for detection of the enzyme production. Both enzymes produced from E. coli were isolated and purified with an Orange A dye resin and FPLC. Their properties were compared with respect to their kinetic parameters, stability, pH profiles, and substrate specificities. Both enzymes have similar k(cat) and K(m) for NeuAc and CTP but different pH profiles. Contrary to the native enzyme, the modified enzyme is more active at higher pH. Studies on specificity indicate that both enzymes have a high specific activity for C-9 modified NeuAc derivatives at neutral pH. Some C-5 modified (hydroxy, deoxy, and deoxyfluoro) NeuAc derivatives are not acceptable as substrates. The modified enzyme has been used in the synthesis of CMP-NeuAc from ManNAc and CMP and sialyl N-acetyllactosamine (Neu-alpha-2,6Gal-beta-1,4GlcNAc) with in situ generation of NeuAc and regeneration of CMP-NeuAc. The 6-O-acyl derivatives of ManNAc were prepared via transesterification in anhydrous dimethylformamide by using an engineered stable subtilisin variant as a catalyst, and the products were used as substrates in sialic acid aldolase-catalyzed synthesis of 9-O-acyl-NeuAc derivatives.
• Scope and limitations of the aldol condensation catalyzed by immobilized acylneuraminate pyruvate lyase
  作者：Claudine Augé、Bénédicte Bouxom、Bertrand Cavayé、Christine Gautheron

  DOI：10.1016/s0040-4039(00)99652-7

  日期：1989.1