3-amino-3-deoxy-D-glucose | 19309-98-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-amino-3-deoxy-D-glucose
• 英文别名: 3-Amino-3-desoxy-D-glucose；kanosamine；3-amino-3-deoxy-D-glucopyranose；(3R,4S,5S,6R)-4-amino-6-(hydroxymethyl)oxane-2,3,5-triol
• CAS: 19309-98-9
• 化学式: C₆H₁₃NO₅
• 分子量: 179.173
• InChiKey: BQCCAEOLPYCBAE-CBPJZXOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  12
• 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：
  116
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-amino-3-deoxy-D-glucose 在 α-lactalbumin 作用下， 以 甲醇 为溶剂， 反应 30.0h， 生成 β,β-D-Gal-(1<->1)-D-Glc3NAc
  参考文献：
  名称：

  A new type of galactosyltransferase reaction: transfer of galactose to the anomeric position of N-acetylkanosamine

  摘要：

  DOI：

  10.1021/ja00059a074
• 作为产物：
  描述：

  尿苷(5')二氢二磷酰(1)-alpha-D-葡萄糖 在 L-谷氨酰胺 、 A_. mediterranei cell-free extract 、 β-烟酰胺腺嘌呤二核苷酸 作用下， 反应 6.0h， 以2%的产率得到3-amino-3-deoxy-D-glucose
  参考文献：
  名称：

  Kanosamine 生物合成：Aminoshikimate 途径的氮原子的可能来源

  摘要：

  掺入氨基莽草酸酯途径的氮原子的生物合成来源一直是一个问题。3-氨基-3-脱氧-D-果糖 6-磷酸先前已被证明是 4-氨基-3,4-二脱氧-D-阿拉伯-庚糖酸 7-磷酸和 3-氨基-5-羟基苯甲酸的前体通过推断的 1-deoxy-1-imino-D-erythrose 4-phosphate 中间体在 Amycolatopsis mediterranei 无细胞提取物中产生酸。这项调查研究了天然产物卡诺胺可能是 3-amino-3-deoxy-D-fructose 6-phosphate 的前体的可能性。卡诺胺 6-磷酸是通过化学酶促途径合成的，并与 D-核糖 5-磷酸和磷酸烯醇丙酮酸一起在无细胞裂解物中孵育。4-氨基-3的形成，观察到4-双脱氧-D-阿拉伯-庚酮糖酸7-磷酸和3-氨基-5-羟基苯甲酸。随后在 A. mediterranei 的无细胞裂解物中孵育谷氨酰胺和 NAD 与 UDP

  DOI：

  10.1021/ja026628m

文献信息

• Aminoglycoside antibiotics as novel anti-infective agents
  申请人：——

  公开号：US20040058880A1

  公开（公告）日：2004-03-25

  This invention relates to novel aminoglycoside compounds having antibacterial and anti-infective activity and to pharmaceutical compositions, methods of making and methods of treatment employing the same.

  这项发明涉及具有抗菌和抗感染活性的新型氨基糖苷化合物，以及包括这些化合物的药物组合物、制备方法和治疗方法。
• Characterization of the Early Stage Aminoshikimate Pathway in the Formation of 3-Amino-5-hydroxybenzoic Acid:  The RifN Protein Specifically Converts Kanosamine into Kanosamine 6-Phosphate
  作者：Kenji Arakawa、Rolf Müller、Taifo Mahmud、Tin-Wein Yu、Heinz G. Floss

  DOI：10.1021/ja0206339

  日期：2002.9.1

  The biosynthesis of 3-amino-5-hydroxybenzoic acid (AHBA), precursor of the ansamycin and mitomycin antibiotics, proceeds by the aminoshikimate pathway from 3,4-dideoxy-4-amino-D-arabino-heptulosonic acid 7-phosphate (aminoDAHP). Identification of RifN, product of one of three genes from the rifamycin biosynthetic gene cluster known to be essential for aminoDAHP formation, as a specific kanosamine

  安沙霉素和丝裂霉素抗生素的前体 3-氨基-5-羟基苯甲酸 (AHBA) 的生物合成通过氨基莽草酸途径从 3,4-二脱氧-4-氨基-D-阿拉伯-庚酮糖酸 7-磷酸 (aminoDAHP ）。鉴定 RifN，利福霉素生物合成基因簇中已知对氨基 DAHP 形成必不可少的三个基因之一的产物，因为特定的卡诺胺（3-脱氧-3-氨基-D-葡萄糖）6-激酶建立卡诺胺及其 6-磷酸盐作为 AHBA 形成的特定中间体。这暗示了氨基 DAHP 形成的假设反应序列，因此是 AHBA 生物合成的早期步骤，从 UDP-D-葡萄糖开始并通过 C-3 处的氧化和转氨作用引入氮。
• Studies of Aminosugars. XVII. Production of 3-Amino-3-deoxy-D-glucose by Bacillus Species
  作者：Sumio Umezawa、Kimio Umino、Seiji Shibahara、Shoji Omoto

  DOI：10.1246/bcsj.40.2419

  日期：1967.10

  3-Amino-3-deoxy-d-glucose was isolated from a fermentation broth of a Bacillus species designated as Bacillus aminoglucosidicus. This demonstrated for the first time the presence of a monosaccharide aminodeoxypyranose in nature. The aminosugar was isolated in a high yield by using column chromatography with cation exchange resin. The identity of the product with 3-amino-3-deoxy-d-glucose was completely established by comparing the natural product and its derivatives with synthetic 3-amino-3-deoxy-d-glucose and its corresponding derivatives in elemental analyses, infrared spectra and mixed melting point determination.

  从一种被命名为氨基葡萄糖芽孢杆菌（Bacillus aminoglucosidicus）的发酵液中分离出了 3-氨基-3-脱氧-d-葡萄糖。这首次证明了自然界中存在单糖氨基脱氧吡喃糖。通过阳离子交换树脂柱层析法，高产分离出了这种氨基糖。通过将天然产物及其衍生物与合成的 3-氨基-3-脱氧-d-葡萄糖及其相应衍生物进行元素分析、红外光谱和混合熔点测定，完全确定了该产品与 3-氨基-3-脱氧-d-葡萄糖的同一性。
• Model for Antibiotic Optimization via Neoglycosylation:  Synthesis of Liponeoglycopeptides Active against VRE
  作者：Byron R. Griffith、Candace Krepel、Xun Fu、Sophie Blanchard、Aqeel Ahmed、Charles E. Edmiston、Jon S. Thorson

  DOI：10.1021/ja068602r

  日期：2007.7.1

  The neoglycosylation of a methoxyamine-appended vancomycin aglycon with all possible N'-decanoylglucopyranose and N'-biphenoylglucopyranose regioisomers led to the production of a focused set of liponeoglycopeptide variants in good yields and with excellent stereoselectivity. High-throughput antibacterial assays employing a unique set of vancomycin-resistant Enterococci faecalis and Enterococci faecium clinical isolates revealed that the nature and regiochemistry of glycosyl lipidation modulated vancomycin-resistent Enterococci potency. In contrast to prior work with lipoglycopeptides, this study reveals the glucose C3' or C4' as the optimal position for neoglycopeptide lipidation. This purely chemical method for the diversification of the glycolipid portion of lipoglycopeptide antibiotics is simple to perform on a large scale, requires minimal synthetic effort in sugar donor preparation, and provides access to highly active antibiotics that are not easily prepared by other state-of-the-art methods.
• Synthesis of Sulfonamide-Bridged Glycomimetics
  作者：Marie Lopez、Laurent F. Bornaghi、Hugues Driguez、Sally-Ann Poulsen

  DOI：10.1021/jo2001269

  日期：2011.5.6

  A flexible and short synthesis of sulfonamide-bridged di-, tri-, tetra-, and octasaccharide glycomimetics was accomplished by reaction of glycosyl thioacetates with amino sugar substrates. The chemistry to incorporate the sulfonamide linker in place of a native O-glycosidic bond was broadly scoped, allowing access to head-to-head (1 <-> 1) and head-to-tail (1 -> 2), (1 -> 3), (1 -> 4), and (1 -> 6) sulfonamide-bridged glycomimetics. The synthesis proceeds with retention of configuration at the anomeric center and is compatible with variable stereochemical arrangements and with acid- and base-labile protecting groups.