N-butyryl α-glucosamine | 15961-60-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-butyryl α-glucosamine
• 英文别名: 2-butyrylamino-2-deoxy-α-D-glucopyranose；2-Butyrylamino-2-desoxy-α-D-glucopyranose；N-[(2S,3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]butanamide
• CAS: 15961-60-1
• 化学式: C₁₀H₁₉NO₆
• 分子量: 249.264
• InChiKey: RPJMPMDUKSRLLF-GRUVDUQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  119
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  丁酸酐 、 D-氨基葡萄糖盐酸盐 在 甲醇 、 silver butyrate 作用下， 生成 N-butyryl α-glucosamine
  参考文献：
  名称：

  Haber; zit.bei Baer, Fortschritte der Chemischen Forschung, 1958, vol. 3, p. 822,849,851

  摘要：

  DOI：

文献信息

• An Enzymatic N‐Acylation Step Enables the Biocatalytic Synthesis of Unnatural Sialosides
  作者：Pedro Laborda、Yong‐Mei Lyu、Fabio Parmeggiani、Ai‐Min Lu、Wen‐Jiao Wang、Ying‐Ying Huang、Kun Huang、Juan Guo、Li Liu、Sabine L. Flitsch、Josef Voglmeir

  DOI：10.1002/anie.201914338

  日期：2020.3.23

  material for many biotechnological products through manipulation of its N-acetyl functionality, which can be cleaved under mild conditions using the enzyme family of de-N-acetylases. However, the chemoselective enzymatic re-acylation of glucosamine derivatives, which can introduce new stable functionalities into chitin derivatives, is much less explored. Herein we describe an acylase (CmCDA from Cyclobacterium

  几丁质是自然界中最丰富和最便宜的生物聚合物之一。几丁质通过操纵其 N-乙酰基官能团已成为许多生物技术产品的宝贵起始材料，可在温和条件下使用去 N-乙酰基酶家族将其裂解。然而，葡糖胺衍生物的化学选择性酶促再酰化可以将新的稳定功能引入几丁质衍生物中，但很少有人探索。在本文中，我们描述了一种酰化酶（来自海洋环杆菌的 CmCDA），其在生理反应条件下催化糖胺与一系列羧酸的 N-酰化。这种生物催化剂通过使用高度选择性的酶级联反应，弥补了将几丁质转化为复杂糖苷（例如 C5 修饰的唾液酸苷）方面的重要空白。
• <i>N</i>-Butyryl Glucosamine Increases Matrix Gene Expression by Chondrocytes
  作者：Mark W. Poustie、John Carran、Kevin McEleney、S. Jeffrey Dixon、Tassos P. Anastassiades、Suzanne M. Bernier

  DOI：10.1124/jpet.104.067769

  日期：2004.11

  Proteoglycan synthesis is dependent on N -acetyl glucosamine (GlcNAc) produced by the hexosamine biosynthetic pathway or obtained exogenously. Although used therapeutically to relieve symptoms of osteoarthritis, the actions of glucosamine and its analogs on cartilage are poorly understood. The purpose of this study was to determine the effects on chondrocytes of N -acylated-glucosamine analogs bearing alkyl chains of different lengths. Chondrocytes isolated from neonatal rat femoral condyles were cultured in the presence of glucosamine analogs. GlcNAc, N -proprionyl glucosamine (GlcNPro), or N -butyryl glucosamine (GlcNBu) did not alter cell number, lactate dehydrogenase release, or metabolic acid production, consistent with lack of cytotoxicity. Treatment of chondrocyte cultures with GlcNBu for 6 days significantly increased levels of type II collagen and aggrecan mRNA as determined by Northern blot analysis. In contrast, GlcNAc and GlcNPro had no significant effect. A significant increase in type II collagen mRNA was induced by GlcNBu within 3 days. GlcNBu did not alter stability of type II collagen mRNA, suggesting it acts on gene transcription. We have previously shown that tumor necrosis factor-α (TNFα) decreases levels of type II collagen mRNA. However, chondrocytes pretreated with GlcNBu maintained type II collagen mRNA at control levels in the presence of TNFα. These results establish that the N -butyrylated analog of glucosamine but not GlcNAc promotes matrix gene expression by chondrocytes. Thus, GlcNBu has the potential for use as a chondro-protective agent in osteoarthritis.

  蛋白多糖的合成依赖于己糖胺生物合成途径产生的或外源获得的 N-乙酰氨基葡萄糖 (GlcNAc)。尽管在治疗上用于缓解骨关节炎的症状，但葡萄糖胺及其类似物对软骨的作用仍知之甚少。本研究的目的是确定带有不同长度烷基链的N-酰化-葡萄糖胺类似物对软骨细胞的影响。从新生大鼠股骨髁中分离的软骨细胞在葡萄糖胺类似物存在下进行培养。 GlcNAc、N-丙酰氨基葡萄糖 (GlcNPro) 或 N-丁酰氨基葡萄糖 (GlcNBu) 不会改变细胞数量、乳酸脱氢酶释放或代谢酸产生，这与缺乏细胞毒性一致。通过 Northern 印迹分析确定，用 GlcNBu 处理软骨细胞培养物 6 天，II 型胶原蛋白和聚集蛋白聚糖 mRNA 的水平显着增加。相比之下，GlcNAc和GlcNPro没有显着影响。 GlcNBu 在 3 天内诱导 II 型胶原 mRNA 显着增加。 GlcNBu 不会改变 II 型胶原 mRNA 的稳定性，表明它作用于基因转录。我们之前已经证明肿瘤坏死因子-α (TNFα) 会降低 II 型胶原蛋白 mRNA 的水平。然而，在 TNFα 存在的情况下，用 GlcNBu 预处理的软骨细胞将 II 型胶原 mRNA 维持在对照水平。这些结果证实，葡糖胺的N-丁酰化类似物而非GlcNAc促进软骨细胞的基质基因表达。因此，GlcNBu 有潜力用作骨关节炎的软骨保护剂。
• Some Fatty Acid Derivatives of D-Glucosamine
  作者：Yoshiyuki Inouye、Konoshin Onodera、Shozaburo Kitaoka、Shigehiro Hirano

  DOI：10.1021/ja01599a051

  日期：1956.9
• Haber; zit.bei Baer, Fortschritte der Chemischen Forschung, 1958, vol. 3, p. 822,849,851
  作者：Haber、zit.bei Baer

  DOI：——

  日期：——