N-hexanoyl glucosamine | 13996-79-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-hexanoyl glucosamine
• 英文别名: N-Hexanoyl-D-glucosamine；N-[(3R,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]hexanamide
• CAS: 13996-79-7
• 化学式: C₁₂H₂₃NO₆
• mdl: MFCD00059806
• 分子量: 277.318
• InChiKey: HXYXZDBHBFMFTN-IZDZDGOPSA-N

物化性质

• 沸点：
  578.6±50.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.916
• 拓扑面积：
  119
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-hexanoyl glucosamine 以 丙酮 为溶剂， 反应 16.75h， 生成
  参考文献：
  名称：

  Miethchen, Ralf; Faltin, Franziska, Journal fur Praktische Chemie - Chemiker-Zeitung, 1998, vol. 340, # 6, p. 544 - 550

  摘要：

  DOI：
• 作为产物：
  描述：

  D-氨基葡萄糖盐酸盐 、 己酸 生成 N-hexanoyl glucosamine
  参考文献：
  名称：

  Synthesis of some p-nitrophenyl 2-acylamino-2-deoxy-d-glucosides and their hydrolysis with the β-d-hexosaminidase from Hohenbuehelia serotina

  摘要：

  DOI：

  10.1016/s0008-6215(00)83565-x

文献信息

• Highly efficient and selective biocatalytic production of glucosamine from chitin
  作者：Y. M. Lv、P. Laborda、K. Huang、Z. P. Cai、M. Wang、A. M. Lu、C. Doherty、L. Liu、S. L. Flitsch、J. Voglmeir

  DOI：10.1039/c6gc02910h

  日期：——

  N-Acetyl glucosamine (GlcNAc) is one of the most abundant biomolecules on Earth and is cheaply available from chitin, a major component of crustaceans.

  N-乙酰氨基葡萄糖（GlcNAc）是地球上最丰富的生物分子之一，可以廉价地从甲壳类动物的主要成分几丁质中获得。
• <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。
• Treatment of arthritis and compositions therefore
  申请人：——

  公开号：US20020045597A1

  公开（公告）日：2002-04-18

  A 2-glucosamine derivative of the general formula (I): 1 wherein R is an alkyl radical of the general formula C n H 2n+1 and n is selected from 2-12; and pharmaceutically acceptable salts, esters and glucosides thereof, used for a treatment in a mammal selected from the group consisting of (a) arthritis, particularly osteoarthritis and inflammatory arthritis; (b) enhancing cartilage formation in a mammal; (c) enhancing chondrocytes cell proliferation; (d) production of glycosaminoglycan in a mammal; and (e) alleviating the symptoms of joint stiffness and restricted mobility.

  通式(I)的 2-氨基葡萄糖衍生物： 1 其中 R 是通式 C 的烷基 n H 2n+1 和 n 选自 2-12；及其药学上可接受的盐、酯和葡萄糖苷，用于治疗选自以下组别的哺乳动物：(a) 关节炎，尤其是骨关节炎和炎症性关节炎；(b) 促进哺乳动物软骨的形成；(c) 促进软骨细胞的增殖；(d) 促进哺乳动物糖胺聚糖的生成；以及 (e) 减轻关节僵硬和活动受限的症状。
• Biological Properties of N-Acyl and N-Haloacetyl Neuraminic Acids: Processing by Enzymes of Sialic Acid Metabolism, and Interaction with Influenza Virus
  作者：A Humphrey

  DOI：10.1016/s0968-0896(02)00213-4

  日期：2002.10

  Several unnatural N-acyl neuraminic acids (N-propionyl, N-hexanoyl, N-benzoyl, N-trifluoroacetyl, N-chloroacetyl, N-difluoroacetyl) were prepared enzymatically using immobilised sialic acid aldolase. N-Trifluoroacetyl- N-chloroacetyl- and N-difluoroacetyl neuraminic acids were shown to enhance up to 10-fold the rate of association of influenza virus A to a sialoglycolipid neomembrane by surface plasmon resonance, and were found to act as weak inhibitors (K-iapp 0.45-2.0 mM) of influenza virus neuraminidase. The N-propionyl, N-chloroacetyl- and N-difluoroacetyl neuraminic acids were found to be substrates for recombinant Escherichia coli CMP sialate synthase, to give the corresponding CMP-N-acyl-neuraminic acids. CMP-N-propionyl neuraminic acid was found not to be a substrate for CMP-N-acetyl neuraminic acid hydroxylase from pig submandibular gland. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis of 2-acylamino-2-deoxy-d-glucofuranoses and their transformation into hex-2-enofuranoses
  作者：José G Fernández-Bolaños、Vı́ctor Ulgar、Inmaculada Robina、José Fuentes

  DOI：10.1016/s0008-6215(99)00225-6

  日期：1999.12

  The preparation of 2-deoxy-2-hexanamido (octanamido, decanamido, dodecanamido)-5,6-isopropylidene-D-glucofuranoses (9-12) from the corresponding O-unprotected 2-acylamino-2-deoxy-D-glucopyranoses through the bicyclic glucofurano[2,1-d]oxazolines is reported. Compounds 9-12 are transformed into 2-acylamino-2-deoxy-2-enofuranoses by treatment with Amberlite IRA-400 (OH-) resin. (C) 1999 Elsevier Science Ltd. All rights reserved.