6-azido-6-deoxy-N-acetyl-D-mannosamine | 146912-87-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-azido-6-deoxy-N-acetyl-D-mannosamine
• 英文别名: ManNAc6N₃；2-Acetamido-6-azido-2,6-dideoxy-d-mannose；N-[(2S,3R,4R,5R)-6-azido-3,4,5-trihydroxy-1-oxohexan-2-yl]acetamide
• CAS: 146912-87-0
• 化学式: C₈H₁₄N₄O₅
• 分子量: 246.223
• InChiKey: ZNNSWWSFZABEFP-WCTZXXKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  121
• 氢给体数：
  4
• 氢受体数：
  7

安全信息

• 储存条件：
  温度：\<0°C，存放在惰性气体中。

反应信息

• 作为反应物：
  描述：

  丙酮酸钠-3-13C 、 6-azido-6-deoxy-N-acetyl-D-mannosamine 在 aldolase 作用下， 以93%的产率得到[3-13C]-5-acetamido-9-azido-3,5,9-trideoxy-D-glycero-D-galacto-2-nonulopyranosonic acid
  参考文献：
  名称：

  Chemoenzymatic Synthesis of the 9-Deoxy- 9-fluoro-[3-¹³C]-NeuAc-α-(2→6)-[U-¹³C]-Gal-β- Sequence on an Intact Glycoprotein

  摘要：

  DOI：

  10.1021/ja982950e
• 作为产物：
  描述：

  5-acetamido-9-azido-3,5,9-trideoxy-D-glycero-D-galacto-2-nonulopyranosonic acid 在 1,4-dihydronicotinamide adenine dinucleotide 、 aldolase 作用下， 以98%的产率得到6-azido-6-deoxy-N-acetyl-D-mannosamine
  参考文献：
  名称：

  Chemoenzymatic Synthesis of the 9-Deoxy- 9-fluoro-[3-¹³C]-NeuAc-α-(2→6)-[U-¹³C]-Gal-β- Sequence on an Intact Glycoprotein

  摘要：

  DOI：

  10.1021/ja982950e

文献信息

• One-pot multi-enzyme (OPME) chemoenzymatic synthesis of sialyl-Tn-MUC1 and sialyl-T-MUC1 glycopeptides containing natural or non-natural sialic acid
  作者：Hamed Malekan、Gabriel Fung、Vireak Thon、Zahra Khedri、Hai Yu、Jingyao Qu、Yanhong Li、Li Ding、Kit S. Lam、Xi Chen

  DOI：10.1016/j.bmc.2013.02.040

  日期：2013.8

  containing naturally occurring and non-natural sialic acids have been chemoenzymatically synthesized from Tn-MUC1 glycopeptide using one-pot multienzyme (OPME) approaches. In situ generation of the sialyltransferase donor cytidine 5′-monophosphate-sialic acid (CMP-Sia) using a CMP-sialic acid synthetase in the presence of an extra amount of cytidine 5′-triphosphate (CTP) and removal of CMP from the

  使用一锅多酶 (OPME) 方法从 Tn-MUC1 糖肽化学酶法合成了一系列含有天然和非天然唾液酸的 STn-MUC1 和 ST-MUC1 糖肽。在额外量的胞苷 5'-三磷酸 (CTP) 存在下使用 CMP-唾液酸合成酶原位生成唾液酸转移酶供体胞苷 5'-单磷酸-唾液酸 (CMP-Sia) 并从反应中去除 CMP混合物通过快速 C18 柱纯化允许完全消耗 Tn-MUC1 糖肽用于 STn-MUC1 的定量合成。甲空肠弯曲杆菌β1-3GalT（CjCgtBΔ30-His的6) 突变体已被发现催化一个或多个半乳糖残基转移到 Tn-MUC1 以合成 T-MUC1 和半乳糖基化的 T-MUC1。使用多杀巴斯德氏菌α2–3-唾液酸转移酶 3 (PmST3) 与脑膜炎奈瑟菌CMP-唾液酸合成酶 (NmCSS) 和大肠杆菌唾液酸醛缩酶在一锅中对 T-MUC1 进行唾液酸化，可有效产生 ST-MUC1。这些糖肽是潜在的癌症疫苗候选物。
• N-acetylated sialic acids and related sialosides
  申请人：The Regents of the University of California

  公开号：US11161868B2

  公开（公告）日：2021-11-02

  The present invention provides N-acetyl derivatives of sialic acids, including N-acetyl derivatives of Neu5Ac and Neu5Gc. Methods for preparing related precursors and a variety of sialosides are also disclosed.

  本发明提供了硅烷酸的 N-乙酰基衍生物，包括 Neu5Ac 和 Neu5Gc 的 N-乙酰基衍生物。本发明还公开了制备相关前体和各种sialosides的方法。
• Sialidase inhibitors and preparation thereof
  申请人：The Regents of the University of California

  公开号：US11325936B2

  公开（公告）日：2022-05-10

  New 2-deoxy-2,3-dehydro-sialic acids and 2,7-anhydro-sialic acids, which are useful as sialidase inhibitors, and enzymatic methods for preparing them are disclosed. The methods include forming a reaction mixture comprising a glycoside acceptor, a sialic acid donor, and a sialyltransferase; maintaining the reaction mixture under conditions sufficient to form a sialoside; and contacting the sialoside with a Streptococcus pneumoniae sialidase to form the sialic acid product. Methods for the inhibition and sialidases and the treatment of cancer and infectious diseases are also disclosed.

  本发明公开了可用作硅糖苷酶抑制剂的新型 2-脱氧-2,3-脱氢-硅酸和 2,7-脱水-硅酸，以及制备它们的酶法。这些方法包括形成一种反应混合物，其中包括糖苷受体、硅烷基酸供体和硅烷基转移酶；将反应混合物保持在足以形成硅烷基苷的条件下；以及将硅烷基苷与肺炎链球菌硅烷基酶接触以形成硅烷基酸产物。此外，还公开了抑制硅烷基糖苷酶以及治疗癌症和传染性疾病的方法。
• An Approach to the Precise Chemoenzymatic Synthesis of ¹³C-Labeled Sialyloligosaccharide on an Intact Glycoprotein:  A Novel One-Pot [3-¹³C]-Labeling Method for Sialic Acid Analogues by Control of the Reversible Aldolase Reaction, Enzymatic Synthesis of [3-¹³C]-NeuAc-α-(2→3)-[U-¹³C]-Gal-β-(1→4)-GlcNAc-β- Sequence onto Glycoprotein, and Its Conformational Analysis by Developed NMR Techniques
  作者：Tatsuo Miyazaki、Hajime Sato、Tohru Sakakibara、Yasuhiro Kajihara

  DOI：10.1021/ja994211j

  日期：2000.6.1

  A one-pot enzymatic C-13-labeling method for the 3-position of sialic acid (NeuAc) analogues has been developed using NeuAc aldolase, lactate dehydrogenase (LDH), alcohol dehydrogenase (ADI-T), and nucleotide pyrophosphatase (NPP). This method consists of two steps, the first of which is degradation to 2-acetamido-2-deoxy-D-mannose (ManNAc) analogues. This degradation reaction was accelerated by a cofactor regeneration system which converts pyruvic acid into lactic acid using LDH, ADH, and beta-nicotinamide adenine dinucleotide oxidized form (beta-NAD(+)). The second step is condensation of the ManNAc analogue with [3-C-13]-pyruvic acid newly added after decomposition of the cofactor by nucleotide pyrophosphatase which play a role like switch to stop conversion of pyruvic acid into lactic acid. Five different NeuAc analogues have been labeled in good yields using this newly developed one-pot enzymatic procedure. Following conversion of [3-C-13]-NeuAc to CMP-[3-C-13]-NeuAc, enzymatic synthesis of [3-C-13]-NeuAc-alpha-(2-->3)-[U-C-13]-Gal-beta-(1-->4)-GlcNAc-beta-x-ovalbumin (x: hybrid type oligosaccharide) 23 and [3-C-13]-NeuAc-alpha-(2-->3)-[U-C-13]-Gal-beta-(1-->4)-GlcNAc-beta-OMe 26 (sialyl LacNAc) was performed using bovine beta-1,4-galactosyltransferase and rat recombinant alpha-2,3-sialyltransferase. The H-1 chemical shifts of all protons in [3-C-13]-NeuAc-alpha-(2-->3)-[U-C-13]-Gal-beta- on a glycoprotein were assigned by 2D HMQC, 1D HSQC-TOCSY, and the herein described 1D and 2D HSQC-TOCSY-NOESY-TOCSY method. More specifically, the 7-, 8-, and 9-protons of NeuAc could be observed by this HSQC-TOCSY-NOESY-TOCSY method even with only a single C-13 atom at the 3-position. In addition, 1D and 2D HMQC-NOESY spectra as well as carbon spin-lattice relaxation times (T-1) were measured to compare the conformational properties and dynamic behavior of the sialylgalactoside as part of the sialyl LacNAc 26 and when bound to a glycoprotein 23. These analyses suggested that the conformational properties of sialyl LacNAc are similar for both the conjugated and unconjugated forms, and that the torsional angle of the sialyl linkage, i.e., COOH-C2(NeuAc)-O-C3(Gal), is biased toward the anti (-146.7 degrees) conformation. In addition, the flexibility of galactosyl ring when bound to a glycoprotein appears to be significantly restricted by the attachment of NeuAc as compared with unconjugated sialyl LacNAc.
• EP0576592A4
  申请人：——

  公开号：EP0576592A4

  公开（公告）日：1996-01-24