5-叠氮-5-脱氧-唾液酸 | 123457-69-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 5-叠氮-5-脱氧-唾液酸
• 英文名称: 5-Azido-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosidonic acid
• 英文别名: 5-azido-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulosonic acid；5-azido-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonic acid；5-azido-3,5-dideoxy-D-glycero-D-galacto-nonulosonic acid；(2S,4S,5R,6R)-5-azido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 123457-69-2
• 化学式: C₉H₁₅N₃O₈
• 分子量: 293.233
• InChiKey: IIBUBQGIILCMTO-YOQZMRDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  162
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5-叠氮-5-脱氧-唾液酸 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-azido-2-deoxy-3,4:5,6-di-O-isopropylidene-aldehydo-D-mannose dimethyl acetal 在 sodium azide 、 硫酸 、 1,4-二巯基-2,3-丁二醇 作用下， 反应 25.0h， 生成 5-叠氮-5-脱氧-唾液酸
  参考文献：
  名称：

  An inexpensive route to 2-azido-2-deoxy-d-mannose and its conversion into an azido analog of N-acetylneuraminic acid

  摘要：

  DOI：

  10.1016/0008-6215(89)84071-6

文献信息

• Microbial Glycosyltransferases for Carbohydrate Synthesis:  α-2,3-Sialyltransferase from <i>Neisseria </i><i>g</i><i>onorrheae</i>
  作者：Masayuki Izumi、Gwo-Jenn Shen、Shirley Wacowich-Sgarbi、Takuji Nakatani、Oliver Plettenburg、Chi-Huey Wong

  DOI：10.1021/ja011382r

  日期：2001.11.1

  exploitation of its substrate specificity and synthetic utility. Several potential acceptor substrates were synthesized in this study, including mono- and oligosaccharides, glycolipids, and glycopeptides and their sulfate derivatives. Some CMP-sialic acid derivatives with modification at the C-5 position were also prepared for evaluation as donor substrates. It was found that the enzyme exhibits a broader

  来自淋病奈瑟菌的 α-2,3-唾液酸转移酶在大肠杆菌中过度生产，以利用其底物特异性和合成效用。本研究合成了几种潜在的受体底物，包括单糖和寡糖、糖脂、糖肽及其硫酸盐衍生物。还制备了一些在 C-5 位进行修饰的 CMP-唾液酸衍生物作为供体底物进行评估。发现与其他唾液酸转移酶相比，该酶表现出更广泛的受体底物特异性，尽管供体特异性非常有限。已证明该酶在代表性唾液酸糖缀合物的制备性合成中的应用。在这项工作和其他人的工作的基础上，
• Schrell, Andreas; Whitesides, George M., Liebigs Annalen der Chemie, 1990, # 11, p. 1111 - 1114
  作者：Schrell, Andreas、Whitesides, George M.

  DOI：——

  日期：——
• 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.
• 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