D-mycaminose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-mycaminose
• 英文别名: Mycaminose,3-Dimethylamino-3.6-didesoxy-D-glucose；Mycaminose；3.6-Dideoxy-3-dimethylamino-D-glucopyranose, Mycaminose；(3R,4S,5S,6R)-4-(dimethylamino)-6-methyloxane-2,3,5-triol
• 化学式: C₈H₁₇NO₄
• 分子量: 191.227
• InChiKey: DIOQKPOBSJVSJS-ZTVVOAFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  73.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  D-mycaminose 、 乙酸酐 在 吡啶 作用下， 生成 1,2,4-tri-O-acetyl-α-D-mycaminose 、 1,2,4-tri-O-acetyl-β-D-mycaminose
  参考文献：
  名称：

  In Vitro Reconstitution of EryCIII Activity for the Preparation of Unnatural Macrolides

  摘要：

  EryCIII is a desosaminyltransferase that converts an inactive macrolide precursor to a biologically active antibiotic. It may have potential for the synthesis of unnatural macrolides with useful biological activities. However, it has been difficult to reconstitute the activity of EryCIII in vitro. We report here that purified, inactive EryCIII can be converted to an active catalyst by the addition of another protein encoded in the same gene cluster, EryCII. The EryCII-treated protein retains activity even when EryCII is removed. We also show that AknT, an activator protein from an unrelated gene cluster, is capable of activating EryCIII. Although the mechanism of activation is not yet understood, we have concluded from these experiments that these antibiotic Gtf activator proteins do not function to deliver substrates to EryCIII and do not exert their effects by forming stable complexes with the Gtf during the glycosyltransfer reaction. We report that activated EryCIII is capable of utilizing an alternative sugar donor, so these results lay the groundwork for the production of novel macrolides.

  DOI：

  10.1021/ja053704n
• 作为产物：
  描述：

  交沙霉丙酯 在 盐酸 作用下， 反应 3.0h， 以67%的产率得到D-mycaminose
  参考文献：
  名称：

  In Vitro Reconstitution of EryCIII Activity for the Preparation of Unnatural Macrolides

  摘要：

  EryCIII is a desosaminyltransferase that converts an inactive macrolide precursor to a biologically active antibiotic. It may have potential for the synthesis of unnatural macrolides with useful biological activities. However, it has been difficult to reconstitute the activity of EryCIII in vitro. We report here that purified, inactive EryCIII can be converted to an active catalyst by the addition of another protein encoded in the same gene cluster, EryCII. The EryCII-treated protein retains activity even when EryCII is removed. We also show that AknT, an activator protein from an unrelated gene cluster, is capable of activating EryCIII. Although the mechanism of activation is not yet understood, we have concluded from these experiments that these antibiotic Gtf activator proteins do not function to deliver substrates to EryCIII and do not exert their effects by forming stable complexes with the Gtf during the glycosyltransfer reaction. We report that activated EryCIII is capable of utilizing an alternative sugar donor, so these results lay the groundwork for the production of novel macrolides.

  DOI：

  10.1021/ja053704n

文献信息

• [EN] SYNTHESIS OF DESOSAMINES<br/>[FR] SYNTHÈSE DE DÉSOSAMINES
  申请人：HARVARD COLLEGE

  公开号：WO2016154533A1

  公开（公告）日：2016-09-29

  The present invention provides desosamine and mycaminose analogs and nitro sugars and methods for their preparation. The invention also provides methods of cyclizing a compound of Formula (Α') with glyoxal to give a nitro sugar of Formula (B). Methods for the preparation of compound of Formula (D') are provided comprising cyclization of a nitro alcohol to give a nitro sugar and reduction and alkylation of the nitro sugar to give a desosamine, mycaminose, or an analog thereof.

  本发明提供了desosamine和mycaminose的类似物以及硝基糖和其制备方法。该发明还提供了将化合物（Α'）与乙二醛环化以给出公式（B）的硝基糖的方法。本发明还提供了制备公式（D'）化合物的方法，其中包括将硝基醇环化以给出硝基糖，并将硝基糖还原和烷基化以给出desosamine、mycaminose或其类似物的方法。
• Synthesis of desosamines
  申请人：President and Fellows of Harvard College

  公开号：US10544182B2

  公开（公告）日：2020-01-28

  The present invention provides desosamine and mycaminose analogs and nitro sugars and methods for their preparation. The invention also provides methods of cyclizing a compound of Formula (A′) with glyoxal to give a nitro sugar of Formula (B). Methods for the preparation of compound of Formula (D′) are provided comprising cyclization of a nitro alcohol to give a nitro sugar and reduction and alkylation of the nitro sugar to give a desosamine, mycaminose, or an analog thereof.

  本发明提供脱糖胺和霉菌胺糖类似物和硝基糖及其制备方法。本发明还提供了式(A′)化合物与乙二醛环化得到式(B)硝基糖的方法。本发明提供了制备式(D′)化合物的方法，包括硝基醇环化得到硝基糖，硝基糖还原和烷基化得到脱糖胺、霉菌胺糖或其类似物。
• SYNTHESIS OF DESOSAMINES
  申请人：President and Fellows of Harvard College

  公开号：US20180111956A1

  公开（公告）日：2018-04-26

  The present invention provides desosamine and mycaminose analogs and nitro sugars and methods for their preparation. The invention also provides methods of cyclizing a compound of Formula (A′) with glyoxal to give a nitro sugar of Formula (B). Methods for the preparation of compound of Formula (D′) are provided comprising cyclization of a nitro alcohol to give a nitro sugar and reduction and alkylation of the nitro sugar to give a desosamine, mycaminose, or an analog thereof.