2-Acetamido-2,4-dideoxy-D-xylo-hexopyranose | 88146-23-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2-Acetamido-2,4-dideoxy-D-xylo-hexopyranose
• 英文别名: N-[(3R,4S,6S)-2,4-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 88146-23-0；88146-25-2；135256-30-3；135256-31-4；135256-32-5；135256-45-0；135256-46-1；135256-47-2；149034-70-8；149063-53-6
• 化学式: C₈H₁₅NO₅
• 分子量: 205.211
• InChiKey: LLRSBEXKLNOWPS-QBARFFCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  99
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-Acetamido-2,4-dideoxy-D-xylo-hexopyranose 在 N-acetylhexosamine kinase 、 5’-三磷酸腺苷 作用下， 反应 19.0h， 以70%的产率得到2-acetamido-2,4-dideoxy-α-D-galactopyranosyl diammonium phosphate
  参考文献：
  名称：

  的底物特异性Ñ朝向-acetylhexosamine激酶Ñ -acetylgalactosamine衍生物

  摘要：

  我们在这里报告细菌N-乙酰己糖胺激酶，NahK，对结构修饰的GalNAc类似物具有广泛的底物特异性，并使用该激酶生产GalNAc-1-磷酸文库。

  DOI：

  10.1016/j.bmcl.2009.07.104
• 作为产物：
  描述：

  (+)-2-acetamido-1,3,6-tri-O-acetyl-2-deoxy-α-D-glucopyranoside 在 甲醇 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium methylate 作用下， 生成 2-Acetamido-2,4-dideoxy-D-xylo-hexopyranose
  参考文献：
  名称：

  Substrate specificity of galactokinase from Streptococcus pneumoniae TIGR4 towards galactose, glucose, and their derivatives

  摘要：

  Galactokinases (GalKs) have attracted significant research attention for their potential applications in the enzymatic synthesis of unique sugar phosphates. The galactokinase (GalKSpe4) cloned from Streptococcus pneumoniae TIGR4 presents a remarkably broad substrate range including 14 diverse natural and unnatural sugars. TLC and MS studies revealed that GalKSpe4 had relaxed activity towards galactose derivatives with modifications on the C-6, 4- or 2-positions. Additionally, GalKSpe4 can also tolerate glucose while glucose derivatives with modifications on the C-6, 4- or 2-positions were unacceptable. More interestingly, GalKSpe4 can phosphorylate L-mannose in moderate yield (43%), while other L-sugars such as L-Gal cannot be recognized by this enzyme. These results are very significant because there is rarely enzyme reported that can phosphorylate such uncommon substrates as L-mannose. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.03.095

文献信息

• Studies on Amino-hexoses. XVI. Synthesis of Deoxy-analogues of<i>N</i>-Acetyl-D-glucosamine
  作者：Hitoshi Arita、Kiyofumi Fukukawa、Yoshio Matsushima

  DOI：10.1246/bcsj.45.3614

  日期：1972.12

  were synthesized by means of chlorination with sulfuryl chloride and reduction of the chlorides with tri-n-butyltin hydride. The free sugars thus obtained failed to crystallize except for 6-deoxy and 4,6-dideoxy compounds. Phenyl glycosides were mostly crystalline. The yield of chlorination and reduction was generally high.

  N-乙酰基-D-氨基葡萄糖的脱氧类似物和苯基N-乙酰基-β-D-氨基葡萄糖的三种脱氧类似物是通过磺酰氯氯化和三正丁基氢化锡还原氯化物合成的。除了6-脱氧和4，6-双脱氧化合物外，由此获得的游离糖没有结晶。苯苷多为结晶。氯化和还原的收率普遍较高。
• Mulzer, Johann; Seilz, Carsten; Luger, Peter, Liebigs Annalen der Chemie, 1991, # 9, p. 947 - 955
  作者：Mulzer, Johann、Seilz, Carsten、Luger, Peter、Weber, Manuela、Reutter, Werner

  DOI：——

  日期：——
• Synthesis of 4-deoxy analogues of 2-acetamido-2-deoxy-d-glucose and 2-acetamido-2-deoxy-d-xylose and their effects on glycoconjugate biosynthesis
  作者：Ali Berkin、Mark A Szarek、Jan Plenkiewicz、Walter A Szarek*、Robert Kisilevsky*

  DOI：10.1016/s0008-6215(99)00314-6

  日期：2000.3

  4-Deoxy analogues of 2-acetamido-2-deoxy-D-glucose and 2-acetamido-2-deoxy-D-xylose were synthesized and evaluated as inhibitors of glycoconjugate biosynthesis. Methyl 2-acetamido-2,4-dideoxy-beta-D-xylo-hexopyranoside (11) showed a reduction in [H-3]GlcN and [C-14]Leu incorporation into hepatocyte cellular glycoconjugates by 89 and 88%, of the control cells, respectively, at 20 mM, whereas the free sugars, 2-acetamido-2,4-dideoxy-alpha,beta-D-xylo-hexopyranoses (15), showed a reduction of [H-3]GlcN and [C-14]Leu incorporation by 75 and 64%, respectively, at 20 mM. The acetylated analogues of 11 and 15, namely methyl 2-acetamido-3,6-di-O-acetyl-2,4-dideoxy-beta-D-xylo-hexopyranoside and 2-acetamido-1.3,6-tri-O-acetyl-2,4-dideoxy-alpha,beta-D-xylo-hexopyranoses, showed a greater inhibition of [H-3]GlcN and [C-14]Leu incorporation at 1 mM compared with their non-acetylated counterparts, but were toxic to hepatocytes at concentrations of 10 and 20 mM. Corresponding derivatives of 2-acetamido-2,4-dideoxy-L-threo-pentopyranose showed no biological effect up to 20 mM, suggesting that the C-6 substituent is important for the biological activity. (C) 2000 Elsevier Science Ltd. All rights reserved.
• MULZER, JOHANN;SEILZ, CARSTEN;LUGER, PETER;WEBER, MANUELA;REUTTER, WERNER, LIEBIGS ANN. CHEM.,(1991) N, C. 947-955
  作者：MULZER, JOHANN、SEILZ, CARSTEN、LUGER, PETER、WEBER, MANUELA、REUTTER, WERNER

  DOI：——

  日期：——
• p-Benzoquinone as precursor for the synthesis of modified d- and l-hexoses: Preparation of 2-acetamido-2,4-dideoxy-d- and l-xylo-hexopyranose
  作者：Jochen Lehmann、Andreas Moritz

  DOI：10.1016/0008-6215(93)84230-4

  日期：1993.2