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GlcNAc-β-SPy

中文名称
——
中文别名
——
英文名称
GlcNAc-β-SPy
英文别名
2-pyridyl 1-thio-2-acetamido-2-deoxy-β-D-glucopyranoside;2-pyridyl 1-thio-N-acetyl-β-D-glucosaminide;N-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-pyridin-2-ylsulfanyloxan-3-yl]acetamide
GlcNAc-β-SPy化学式
CAS
——
化学式
C13H18N2O5S
mdl
——
分子量
314.362
InChiKey
TUXIWGBKMLXVNG-WECGXBHGSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    -0.4
  • 重原子数:
    21
  • 可旋转键数:
    4
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.54
  • 拓扑面积:
    137
  • 氢给体数:
    4
  • 氢受体数:
    7

反应信息

  • 作为反应物:
    描述:
    GlcNAc-β-SPy 、 GalN-HCl-β-DMT 在 exo-β-D-glucosaminidase from Amycolatopsis orientalis 作用下, 以 aq. buffer 为溶剂, 以7%的产率得到GalNβ1→4GlcNAc-β-SPy
    参考文献:
    名称:
    4,6-Dimethoxy-1,3,5-triazin-2-yl β-d-glycosaminides: Novel Substrates for Transglycosylation Reaction Catalyzed by Exo-β-d-glucosaminidase fromAmycolatopsis orientalis
    摘要:
    A novel sugar adduct, 4,6-dimethoxy-1,3,5-triazin-2-yl beta-D-glucosaminide (GlcN-beta-DMT), has been prepared by the reaction of D-glucosamine (GlcN) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-morpholinium chloride (DMT-MM). The adduct was recognized by exo-beta-D-glucosaminidase (GlcNase) from Amycolatopsis orientalis and transferred the GlcN moiety, giving rise to the corresponding glucosaminides. This chemo-enzymatic process was successfully applied to D-galactosamine (GalN). GalN-beta-DMT prepared directly from GalN and DMT-MM behaved as an efficient glycosyl donor for transfer of the GalN moiety catalyzed by the same enzyme. The introduction of the 4,6-dimethoxy-1,3,5-triazin-2-yl leaving group to the anomeric center significantly enhanced transglycosylating ability, resulting in the efficient glycosidase-catalyzed synthesis of glycosaminides.
    DOI:
    10.1080/07328303.2012.698437
  • 作为产物:
    描述:
    [(2R,3S,4R,5R,6S)-5-乙酰氨基-3-乙酰氧基-2-(乙酰氧基甲基)-6-吡啶-2-基硫基四氢吡喃-4-基]乙酸酯 在 sodium methylate 作用下, 以 甲醇二氯甲烷 为溶剂, 反应 1.0h, 以95%的产率得到GlcNAc-β-SPy
    参考文献:
    名称:
    C-连接的透明质酸二糖模拟物的合成。
    摘要:
    描述了设计为模仿透明质酸的重复单元二糖的C-二糖的合成。通过砜,2-乙酰氨基-4,6-O-亚苄基-3-O-叔丁基二甲基甲硅烷基-1,2-二脱氧-1-吡啶基磺酰基-β-D的SmI2促进的偶联反应获得目标化合物-吡喃葡萄糖(6),和醛,对甲氧基苯基2,3-二-O-苄基-4-脱氧-4-C-甲酰基-6-Op-甲氧基苄基-β-D-吡喃葡萄糖苷(14)。
    DOI:
    10.1016/j.carres.2007.05.031
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文献信息

  • 4,6-Dimethoxy-1,3,5-triazin-2-yl β-d-glycosaminides: Novel Substrates for Transglycosylation Reaction Catalyzed by Exo-β-d-glucosaminidase from<i>Amycolatopsis orientalis</i>
    作者:Tomonari Tanaka、Tomonori Wada、Masato Noguchi、Masaki Ishihara、Atsushi Kobayashi、Takayuki Ohnuma、Tamo Fukamizo、Ryszard Brzezinski、Shin-ichiro Shoda
    DOI:10.1080/07328303.2012.698437
    日期:2012.10
    A novel sugar adduct, 4,6-dimethoxy-1,3,5-triazin-2-yl beta-D-glucosaminide (GlcN-beta-DMT), has been prepared by the reaction of D-glucosamine (GlcN) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-morpholinium chloride (DMT-MM). The adduct was recognized by exo-beta-D-glucosaminidase (GlcNase) from Amycolatopsis orientalis and transferred the GlcN moiety, giving rise to the corresponding glucosaminides. This chemo-enzymatic process was successfully applied to D-galactosamine (GalN). GalN-beta-DMT prepared directly from GalN and DMT-MM behaved as an efficient glycosyl donor for transfer of the GalN moiety catalyzed by the same enzyme. The introduction of the 4,6-dimethoxy-1,3,5-triazin-2-yl leaving group to the anomeric center significantly enhanced transglycosylating ability, resulting in the efficient glycosidase-catalyzed synthesis of glycosaminides.
  • Synthesis of a C-linked hyaluronic acid disaccharide mimetic
    作者:Zhong-Xu Ren、Qiang Yang、Kenneth N. Price、Tianniu Chen、Cara Nygren、John F.C. Turner、David C. Baker
    DOI:10.1016/j.carres.2007.05.031
    日期:2007.9
    The synthesis of a C-disaccharide that is designed as a mimetic for the repeating unit disaccharide of hyaluronic acid is described. The target compound was obtained via the SmI2-promoted coupling reaction of the sulfone, 2-acetamido-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1,2-dideoxy-1-pyridinyl sulfonyl-beta-D-glucopyranose (6), and the aldehyde, p-methoxyphenyl 2,3-di-O-benzyl-4-deoxy-4-C
    描述了设计为模仿透明质酸的重复单元二糖的C-二糖的合成。通过砜,2-乙酰氨基-4,6-O-亚苄基-3-O-叔丁基二甲基甲硅烷基-1,2-二脱氧-1-吡啶基磺酰基-β-D的SmI2促进的偶联反应获得目标化合物-吡喃葡萄糖(6),和醛,对甲氧基苯基2,3-二-O-苄基-4-脱氧-4-C-甲酰基-6-Op-甲氧基苄基-β-D-吡喃葡萄糖苷(14)。
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