2-amino-2-deoxy-β-D-glucopyranose 6-sulfate | 161642-81-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-amino-2-deoxy-β-D-glucopyranose 6-sulfate
• 英文别名: glucosamine-6-sulphate；glucosamine 6-O-sulfate；D-glucosamine 6-sulfate；β-D-glucosamine-6-O-sulfate；GlcN-6S；Glucosamine 6-sulfate；[(2R,3S,4R,5R,6R)-5-amino-3,4,6-trihydroxyoxan-2-yl]methyl hydrogen sulfate
• CAS: 161642-81-5
• 化学式: C₆H₁₃NO₈S
• 分子量: 259.237
• InChiKey: MTDHILKWIRSIHB-QZABAPFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  168
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 2-amino-2-deoxy-β-D-glucopyranose 6-sulfate 在 吡啶 作用下， 反应 12.0h， 生成 Acetic acid (2S,3R,4R,5S,6R)-2,5-diacetoxy-3-acetylamino-6-sulfooxymethyl-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Sulphated Mucin Oligosaccharides from Porcine Small Intestine Analysed by Four-Sector Tandem Mass Spectrometry

  摘要：

  The fraction of sulphated oligosaccharide alditols isolated from mucin glycopeptides of porcine small intestine 'insoluble' mucin complex was analysed by negative-ion fast atom bombardment (FAB) tandem mass spectrometry. Collision-induced dissociation (CID) tandem mass spectra of native and peracetylated species were compared with standards of sulphated monosaccharides. The tandem mass spectra revealed structural information of the carbohydrate sequence and sulphate position. Negative-ion FAB ionization of the peracetylated sulphated oligo-saccharide alditols was at least three times more sensitive than that of the native sulphated oligosaccharide alditols, as revealed by comparing the signal-to-noise ratios, and allowed the detection of eleven compared with six pseudo-molecular ions. Fourteen structures were determined from the CID tandem mass spectra obtained. The main sulphation site was C-6 of an N-acetylglucosamine 6-linked to the N-acetylgalactosaminitol. C-3 of the N-acetylgalactosaminitol could be unsubstituted or extended with a series of up to three monosaccharide residues including blood group H determinants and blood group A determinants. Also, the sulphated N-acetylglucosamine could be further extended. The most abundant structure was a monosulphated trisaccharide with the sequence Gal-->3(SO3-->6GlcNAc-->6)GalNAcol. The sulphation at C-6 of N-acetylglucosamine seems to be a common feature for O-linked oligosaccharides, and has been described both for skeletal keratan sulphates and respiratory mucin oligosaccharides. Low-abundance ions were also detected from oligosaccharides with sulphation at C-3 of an amino sugar residue. This seems to be a novel sulphation site for mucin oligosaccharides.

  DOI：

  10.1002/(sici)1096-9888(199605)31:5<560::aid-jms331>3.0.co;2-0
• 作为产物：
  描述：

  D-glucosamine hydrochloride 在 pyridine-SO3 complex 作用下， 以 formamide 为溶剂， 反应 4.0h， 生成 2-amino-2-deoxy-β-D-glucopyranose 6-sulfate
  参考文献：
  名称：

  Glucosamine sulfate promotes osteoblastic differentiation of MG-63 cells via anti-inflammatory effect

  摘要：

  Glucosamine sulfate (SGlc) has been known to be effective in controlling osteoarthritis (OA) symptoms in several clinical studies. However, the mechanisms of this positive effect of SGlc in human OA still remain elusive. Therefore, first, the effects of SGlc on the differentiation of osteoblast-like MG-63 cells were investigated. Our results demonstrate that SGlc can increase ALP activity, collagen synthesis, osteocalcin secretion, and mineralization in osteoblastic cells in vitro. Furthermore, it was observed that SGlc exhibited anti-inflammatory effect on production of TNF-alpha, IL-1 beta, and PGE(2) in macrophage, RAW264.7 cells. In conclusion, these results suggest that SGlc can promote cell differentiation in cultured MG-63 osteoblast cells via anti-inflammatory effect. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.01.030

文献信息

• Inorganic-organic hybrid compound
  申请人：Karlsruher Institut für Technologie

  公开号：US20170112948A1

  公开（公告）日：2017-04-27

  The present invention relates to an inorganic-organic hybrid compound as ionic compound, composed of an inorganic cation and of an organic active ingredient anion and also, optionally, of an organic fluorescent dye anion.
• Glucosamine sulfate promotes osteoblastic differentiation of MG-63 cells via anti-inflammatory effect
  作者：Moon Moo Kim、Eresha Mendis、Niranjan Rajapakse、Se-Kwon Kim

  DOI：10.1016/j.bmcl.2007.01.030

  日期：2007.4

  Glucosamine sulfate (SGlc) has been known to be effective in controlling osteoarthritis (OA) symptoms in several clinical studies. However, the mechanisms of this positive effect of SGlc in human OA still remain elusive. Therefore, first, the effects of SGlc on the differentiation of osteoblast-like MG-63 cells were investigated. Our results demonstrate that SGlc can increase ALP activity, collagen synthesis, osteocalcin secretion, and mineralization in osteoblastic cells in vitro. Furthermore, it was observed that SGlc exhibited anti-inflammatory effect on production of TNF-alpha, IL-1 beta, and PGE(2) in macrophage, RAW264.7 cells. In conclusion, these results suggest that SGlc can promote cell differentiation in cultured MG-63 osteoblast cells via anti-inflammatory effect. (c) 2007 Elsevier Ltd. All rights reserved.
• Sulphated Mucin Oligosaccharides from Porcine Small Intestine Analysed by Four-Sector Tandem Mass Spectrometry
  作者：Niclas G. Karlsson、Hasse Karlsson、Gunnar C. Hansson

  DOI：10.1002/(sici)1096-9888(199605)31:5<560::aid-jms331>3.0.co;2-0

  日期：1996.5

  The fraction of sulphated oligosaccharide alditols isolated from mucin glycopeptides of porcine small intestine 'insoluble' mucin complex was analysed by negative-ion fast atom bombardment (FAB) tandem mass spectrometry. Collision-induced dissociation (CID) tandem mass spectra of native and peracetylated species were compared with standards of sulphated monosaccharides. The tandem mass spectra revealed structural information of the carbohydrate sequence and sulphate position. Negative-ion FAB ionization of the peracetylated sulphated oligo-saccharide alditols was at least three times more sensitive than that of the native sulphated oligosaccharide alditols, as revealed by comparing the signal-to-noise ratios, and allowed the detection of eleven compared with six pseudo-molecular ions. Fourteen structures were determined from the CID tandem mass spectra obtained. The main sulphation site was C-6 of an N-acetylglucosamine 6-linked to the N-acetylgalactosaminitol. C-3 of the N-acetylgalactosaminitol could be unsubstituted or extended with a series of up to three monosaccharide residues including blood group H determinants and blood group A determinants. Also, the sulphated N-acetylglucosamine could be further extended. The most abundant structure was a monosulphated trisaccharide with the sequence Gal-->3(SO3-->6GlcNAc-->6)GalNAcol. The sulphation at C-6 of N-acetylglucosamine seems to be a common feature for O-linked oligosaccharides, and has been described both for skeletal keratan sulphates and respiratory mucin oligosaccharides. Low-abundance ions were also detected from oligosaccharides with sulphation at C-3 of an amino sugar residue. This seems to be a novel sulphation site for mucin oligosaccharides.