β-D-fructofuranosyl-(2->1)-2-acetamido-2-deoxy-α-D-glucopyranoside | 84039-32-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-fructofuranosyl-(2->1)-2-acetamido-2-deoxy-α-D-glucopyranoside
• 英文别名: β-D-fructofuranosyl-(2→1)-2-acetamido-2-deoxy-α-D-glucopyranoside；β-D-fructofuranosyl-(2↔1)-2-acetamido-2-deoxy-α-D-glucopyranoside；(2-acetamido-2-deoxy-α-D-glucopyranosyl)-(1→2)-β-D-fructofuranose；2-acetamido-2-deoxy-α-D-glucopyranosyl-β-D-fructofuranoside；N-Acetylsucrosamine；(2-Acetamido-2-deoxy-alpha-d-glucopyranosyl)-(1-->2)-beta-d-fructofuranose；N-[(2R,3R,4R,5S,6R)-2-[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 84039-32-7
• 化学式: C₁₄H₂₅NO₁₁
• 分子量: 383.353
• InChiKey: BSLNOSDWGPTRMK-PAZNGLBGSA-N

物化性质

• 沸点：
  801.9±65.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  198
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  β-D-fructofuranosyl-(2->1)-2-acetamido-2-deoxy-α-D-glucopyranoside 在 β-fructofuranosidases from Mycelia of Aspergillus oryzae 作用下， 以 aq. buffer 为溶剂， 反应 8.0h， 生成 β-D-fructofuranosyl-(2→1)-β-D-fructofuranosyl-(2↔1)-2-acetamido-2-deoxy-α-D-glucopyranoside 、 β-D-fructofuranosyl-(2→1)-β-D-fructofuranosyl-(2→1)-β-D-fructofuranosyl-(2↔1)-2-acetamido-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  使用米曲霉中的β-果糖呋喃糖苷酶从N-乙酰基蔗糖酶合成新型寡糖。

  摘要：

  米曲霉NBRC100959的菌丝体含有两种类型的β-果糖呋喃糖苷酶，反式果糖基化催化酶（βFFaseI）和水解催化酶（betaFFaseII）。使用从NBRC100959菌丝体中提取的betaFFaseI，由GlcNAc和果糖组成的两种新型寡糖，即β-d-果糖呋喃糖基-（2-> 1）-β-d-果糖呋喃糖基-（2 <-> 1）-2-乙酰胺基-2-脱氧γ-α-d-吡喃葡萄糖苷（N-乙酰基-1-酮糖胺，1-KesNAc）和β-d-果糖呋喃糖基-（2-> 1）-β-d-果糖呋喃糖基-（2--由β-d-果糖呋喃糖基-合成> 1）-β-d-果糖呋喃基syl-（2-> 1）-2-乙酰胺基-2-脱氧-α-d-吡喃葡萄糖苷（N-乙酰基丝氨酰胺，NysNAc）。 （2→1）-2-乙酰氨基-2-脱氧-α-d-吡喃葡萄糖苷（N-乙酰基糖胺，SucNAc）。接下来，我们计划使用A合成1-KesNAc和NysNAc。

  DOI：

  10.1016/j.carres.2013.10.006
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitroanilino)-α-D-glucopyranosyl bromide 在 钯 三苄胺 、 氢气 、 sodium methylate 、 silver perchlorate 作用下， 以 甲醇 、 水 、 溶剂黄146 、 苯 为溶剂， 反应 24.0h， 生成 β-D-fructofuranosyl-(2->1)-2-acetamido-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of 2-amino-2-deoxy-α-d-glucopyranosyl β-d-fructofuranoside (2-amino-2-deoxysucrose) via Koenigs-Knorr reaction

  摘要：

  DOI：

  10.1016/0008-6215(82)84045-7

文献信息

• The Donor Substrate Spectrum of Recombinant Sucrose Synthase 1 from Potato for the Synthesis of Sucrose Analogues
  作者：Ulrike Römer、Carsten Rupprath、Lothar Elling

  DOI：10.1002/adsc.200303015

  日期：2003.6

  The donor substrate spectrum of recombinant sucrose synthase 1 (SuSy1) from potato was studied in order to synthesise novel sucrose analogues. With D-fructose as acceptor substrate SuSy1 accepts a variety of UDP-activated sugars, e.g., UDP-N-acetyl-α-D-glucosamine (UDP-GlcNAc, 2) (100%), UDP-α-D-glucuronic acid (UDP-GlcA, 3) (32%), UDP-α-D-xylose (UDP-Xyl, 4) (39%), UDP-α-D-galactose (UDP-Gal, 5) (23%)

  为了合成新型蔗糖类似物，研究了马铃薯中重组蔗糖合酶1（SuSy1）的供体底物谱。以D-果糖为受体底物，SuSy1可以接受多种UDP活化的糖，例如UDP- N-乙酰基-α-D-葡萄糖胺（UDP-GlcNAc，2）（100％），UDP-α-D-葡萄糖醛酸（UDP-GlcA，3）（32％），UDP-α-D-木糖（UDP-Xyl，4）（39％），UDP-α-D-半乳糖（UDP-Gal，5）（23％），和UDP- N-乙酰基-α-D-半乳糖胺（UDP-GalNAc，6）（23％）。动力学分析表明，非天然供体2（k cat / K m 1.2 s -1  mM -1）和5（k cat / K m 0.01 s -1  mM -1）与UDP-Glc 1（k cat / K m 310.4 s -1  mM -1）相较较差。UDP-GlcNAc用于制备合成中，产生188 mg（0.5 mmol）2-乙酰氨
• Enzymatic synthesis of novel oligosaccharides from <i>N</i>-acetylsucrosamine and melibiose using <i>Aspergillus niger</i> α-galactosidase, and properties of the products
  作者：Yohei Sakaki、Mitsuru Tashiro、Moe Katou、Chiseko Sakuma、Takako Hirano、Wataru Hakamata、Toshiyuki Nishio

  DOI：10.1080/09168451.2016.1189316

  日期：2016.9.1

  (RafNAc) and N-acetylplanteosamine (PlaNAc), were synthesized from N-acetylsucrosamine and melibiose using the transgalactosylation activity of Aspergillus niger α-galactosidase. RafNAc and PlaNAc are novel trisaccharides in which d-glucopyranose residues in raffinose (Raf) and planteose are replaced with N-acetyl-d-glucosamine. These trisaccharides were more stable in acidic solution than Raf. RafNAc

  利用黑曲霉α-半乳糖苷酶的反式半乳糖基化活性，由N-乙酰基蔗糖胺和黑豆糖合成了两种寡糖N-乙酰基raffinosamine（RafNAc）和N-乙酰基植物糖胺（PlaNAc）。RafNAc和PlaNAc是新型三糖，其中棉子糖（Raf）和植物糖中的d-吡喃葡萄糖残基被N-乙酰基-d-葡萄糖胺替代。这些三糖在酸性溶液中比Raf更稳定。RafNAc被生咖啡豆的α-半乳糖苷酶水解的速度比Raf快。相反，尽管Raf被该酶很好地水解，但是RafNAc没有被酿酒酵母转化酶水解。这些结果表明，RafNAc的理化性质和空间结构与Raf有很大不同。
• Lichtenthaler, Frieder W.; Immel, Stefan; Pokinskyj, Peter, Liebigs Annalen, 1995, # 11, p. 1939 - 1948
  作者：Lichtenthaler, Frieder W.、Immel, Stefan、Pokinskyj, Peter

  DOI：——

  日期：——
• Synthesis of β-d-fructofuranosyl-(2→1)-2-acetamido-2-deoxy-α-d-glucopyranoside (N-acetylsucrosamine) using β-fructofuranosidase-containing Aspergillus oryzae mycelia as a whole-cell catalyst
  作者：Takako Hirano、Toru Wada、Sumire Iwai、Hitoshi Sato、Makoto Noda、Mai Juami、Masatoshi Nakamura、Yasuko Kumaki、Wataru Hakamata、Toshiyuki Nishio

  DOI：10.1016/j.carres.2012.03.037

  日期：2012.5

  Using soft granules consisting of Celite 535 and dried Aspergillus oryzae NBRC100959 mycelia containing beta-fructofuranosidase as a whole-cell catalyst, N-acetylsucrosamine [beta-D-fructofuranosyl-(2 -> 1)-2-acetamido-2-deoxy-alpha-D-glucopyranoside] was produced from sucrose and 2-acetamido-2-deoxy-D-glucose by enzymatic transfructosylation. The isolated yield of N-acetylsucrosamine from the reaction mixture was 22.1% (from sucrose). The result of N-terminal amino acid sequence analysis indicated that the enzyme involved in the synthesis of N-acetylsucrosamine is a product from gene (NCBI accession number; NW_001884675, locus tag; AOR_1_1114084) encoding putative beta-fructofuranosidase on chromosome 6 of strain NBRC100959. The N-acetylsucrosamine we produced is highly soluble in water and is more stable in acidic solution than sucrose. The disaccharide was also produced using dried mycelia prepared from another A. oryzae strains. (C) 2012 Elsevier Ltd. All rights reserved.
• Enzymatic synthesis and the structure elucidation of novel trisaccharides comprised of D-galactose, <i>N-</i>acetyl-D-glucosamine, and D-fructose
  作者：Mitsuru Tashiro、Takashi Fujimoto、Kazuo Furihata、Yohei Sakaki、Takako Hirano、Wataru Hakamata、Toshiyuki Nishio

  DOI：10.1080/07328303.2016.1270296

  日期：2016.9.1

  Enzymatic synthesis of trisaccharides from N-acetylsucrosamine and lactose utilizing the transgalactosylation activity of Aspergillus oryzae -galactosidase provided two reaction products. Structure analyses by various 2D NMR spectroscopy and MS indicated that the products were -D-fructofuranosyl -D-galactopyranosyl-(16)-2-acetamido-2-deoxy--D-glucopyranoside and -D-galactopyranosyl-(16)--D-fructofuranosyl-(21)-2-acetamido-2-deoxy--D-glucopyranoside. Moreover, J-resolved-HMBC experiments indicated that the conformations around the glycosidic bonds of these trisaccharides were very similar. Examination about the pH and thermal stabilities of the glycosidic bonds in the GlcNAc-Fru moiety of the two trisaccharides indicated apparent difference.[GRAPHICS].