2,4,6-trihydroxyacetophenone 3-C-β-D-glucopyranoside | 88885-07-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4,6-trihydroxyacetophenone 3-C-β-D-glucopyranoside
• 英文别名: 3-C-β-D-glucopyranosylphloroacetophenone；3'-(C-β-D-glucosyl)-2',4',6'-trihydroxyacetophenone；1-(3-I(2)-D-Glucopyranosyl-2,4,6-trihydroxyphenyl)ethanone；1-[2,4,6-trihydroxy-3-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]phenyl]ethanone
• CAS: 88885-07-8
• 化学式: C₁₄H₁₈O₉
• 分子量: 330.292
• InChiKey: IWMUXTZLTOTAQO-MMKBDJJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  168
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,4,6-trihydroxyacetophenone 3-C-β-D-glucopyranoside 在 对甲苯磺酸 作用下， 以 水 为溶剂， 反应 72.0h， 以35%的产率得到(2S,3'S,4'R,5'R)-7-acetyl-3',4',5',6'-tetrahydrospiro(benzofuran-2(3H),2'-[2H]pyran)-3',4,4',5',6-pentaol
  参考文献：
  名称：

  β-dC-吡喃葡萄糖基苯乙酮转化为螺酮化合物

  摘要：

  摘要在催化量的p-TsOH存在下，对水中的β-d-C-吡喃葡萄糖基苯乙酮进行处理，得到了螺酮体产品。这是在芳基C-糖苷中环转化的首次证明。通过1H-1H COSY，HMQC，HMBC，NOESY以及相应乙酰化化合物的单晶X射线分析确定产物的结构。

  DOI：

  10.1016/s0008-6215(98)00067-6
• 作为产物：
  描述：

  2,3,4,6-四-O-苄基-α-D-吡喃葡萄糖酰氟 在 palladium on activated charcoal 4 A molecular sieve 、 三氟化硼乙醚 、 氢气 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 24.0h， 生成 2,4,6-trihydroxyacetophenone 3-C-β-D-glucopyranoside
  参考文献：
  名称：

  Regioselective acetyl transfer from the aglycon to the sugar in C-glycosylic compounds facilitated by silica gel

  摘要：

  2'-O-Acetyl C-glycosylic compounds (C-glycosides) were prepared via regioselective acetyl transfer from aglycons to sugar moieties with silica gel in the presence of unprotected primary and secondary hydroxyl groups. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00140-8

文献信息

• Probing the Catalytic Promiscuity of a Regio- and Stereospecific C-Glycosyltransferase from<i>Mangifera indica</i>
  作者：Dawei Chen、Ridao Chen、Ruishan Wang、Jianhua Li、Kebo Xie、Chuancai Bian、Lili Sun、Xiaolin Zhang、Jimei Liu、Lin Yang、Fei Ye、Xiaoming Yu、Jungui Dai

  DOI：10.1002/anie.201506505

  日期：2015.10.19

  The catalytic promiscuity of the novel benzophenone C‐glycosyltransferase, MiCGT, which is involved in the biosynthesis of mangiferin from Mangifera indica, was explored. MiCGT exhibited a robust capability to regio‐ and stereospecific C‐glycosylation of 35 structurally diverse druglike scaffolds and simple phenolics with UDP‐glucose, and also formed O‐ and N‐glycosides. Moreover, MiCGT was able to

  探索了新型二苯甲酮C-糖基转移酶MiCGT的催化混杂性，该酶参与了印度芒果（Mangifera indica）的芒果苷的生物合成。MiCGT对35种结构多样的药物样支架和带有UDP-葡萄糖的简单酚类化合物具有较强的区域和立体特异性C-糖基化能力，还形成了O-和N-糖苷。而且，MiCGT能够用UDP木糖生成C-木糖苷。还利用MiCGT的OGT可逆性与简单的糖供体一起生成C-葡萄糖苷。三种芳基C-糖苷显示出有效的SGLT2抑制活性，IC 50 值为2.6×，7.6×和7.6×10 -7  M， 分别。这些发现首次证明了通过酶法在药物发现中通过对生物活性天然和非天然产物进行C-糖基化来实现多元化的巨大潜力。
• Practical Synthesis of a<i>C</i>-Glycosyl Flavonoid via<i>O</i>→<i>C</i>Glycoside Rearrangement
  作者：Toshihiro Kumazawa、Kazuhito Ohki、Mitsuo Ishida、Shingo Sato、Jun-ichi Onodera、Shigeru Matsuba

  DOI：10.1246/bcsj.68.1379

  日期：1995.5

  The C-glycosylation of 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl fluoride and 2-acetylphloroglucinol 3,5-bis(alkyl ether) in the presence of boron trifluoride etherate as an activator stereoselectively gave the β-C-glucoside in a good yield via O → C glycoside rearrangement. Subsequently, aldol condensation of the C-glucoside with benzaldehyde afforded the corresponding β-C-glucosyl chalcone in a good

  2,3,4,6-四-O-苄基-α-D-吡喃葡萄糖基氟和2-乙酰间苯三酚3,5-双（烷基醚）在三氟化硼醚化物作为活化剂存在下的C-糖基化立体选择性地得到通过 O → C 糖苷重排，β-C-糖苷的产率很高。随后，C-葡萄糖苷与苯甲醛的羟醛缩合以良好的收率提供相应的β-C-葡萄糖基查耳酮。
• DIRECT CONDENSATION OF POLYHYDRIC PHENOLS WITH GLUCOSE
  作者：Jun-ichi Onodera、Mltsuru Takano、Yuji Kishi、Noriko Yokoyama、Ryosuke Ishida

  DOI：10.1246/cl.1983.1487

  日期：1983.10.5

  Acid-catalyzed direct condensation reaction of polyhydric phenols with free glucose in DMSO gave O-α-D-glucopyranoside in preference to its β-anomer; however, phloroglucinol and phloroacetophenone gave C-β-D-glucopyranoside instead.

  多羟基酚与游离葡萄糖在 DMSO 中的酸催化直接缩合反应得到 O-α-D-吡喃葡萄糖苷优先于其 β-端基异构体；然而，间苯三酚和间苯二酚产生了 C-β-D-吡喃葡萄糖苷。
• Functional Characterization and Structural Basis of an Efficient Di-<i>C</i>-glycosyltransferase from <i>Glycyrrhiza glabra</i>
  作者：Meng Zhang、Fu-Dong Li、Kai Li、Zi-Long Wang、Yu-Xi Wang、Jun-Bin He、Hui-Fei Su、Zhong-Yi Zhang、Chang-Biao Chi、Xiao-Meng Shi、Cai-Hong Yun、Zhi-Yong Zhang、Zhen-Ming Liu、Liang-Ren Zhang、Dong-Hui Yang、Ming Ma、Xue Qiao、Min Ye

  DOI：10.1021/jacs.9b12211

  日期：2020.2.19

  A highly efficient di-C-glycosyltransferase GgCGT was discovered from the medicinal plant Glycyrrhiza glabra. GgCGT catalyzes a two-step di-C-glycosylation of flopropione-containing substrates with conversion rates of >98%. To elucidate the catalytic mechanisms of GgCGT, we solved its crystal structures in complex with UDP-Glc, UDP-Gal, UDP/phloretin, and UDP/nothofagin, respectively. Structural analysis

  从药用植物光果甘草中发现了一种高效的二-C-糖基转移酶GgCGT。GgCGT 催化含氟丙酮底物的两步二 C-糖基化，转化率 >98%。为了阐明 GgCGT 的催化机制，我们分别解析了其与 UDP-Glc、UDP-Gal、UDP/根皮素和 UDP/nothofagin 复合物的晶体结构。结构分析表明，糖供体选择性受糖羟基与 D390 和其他关键残基的氢键相互作用控制。GgCGT 的二 C 糖基化能力归因于宽敞的底物结合隧道，G389K 突变可以将二 C 糖基化转换为单 C 糖基化。GgCGT 是第一个具有晶体结构的双 C-糖基转移酶，以及第一个含有糖受体的复杂结构的C-糖基转移酶。这项工作有利于开发有效的生物催化剂，以合成具有药用潜力的 C-糖苷。
• Tannins and Related Compounds. CXXIII. Chromone, Acetophenone and Phenylpropanoid Glycosides and Their Galloyl and /or Hexahydroxydiphenoyl Esters from the Leaves of Syzygium aromaticum MERR. et PERRY.
  作者：Takashi TANAKA、Yuriko ORII、Gen-ichiro NONAKA、Itsuo NISHIOKA

  DOI：10.1248/cpb.41.1232

  日期：——

  From the dried leaves of Syzygium aromaticum MERR. et PERRY (Myrtaceae), eleven new compounds, i.e., eugenol 4-O-β-D-(6'-O-galloyl)glucopyranoside (17), 2-methyl-5, 7-dihydroxychromone 8-C-β-D-glucopyranoside (18) and its 6'-O-gallate (19), 2, 4, 6-trihydroxyacetophenone 3-C-β-D-glucopyranoside (20) and its 2'-O- (21), 6'-O- (22), 2', 3'-di-O- (23), 2', 6'-di-O- (24), 2', 3', 6'-tri-O- (25), 2', 3', 4', 6'-tetra-O-gallate (26) and 2', 3'-di-O-galloyl-4', 6'-O-(S)-hexahydroxydiphenoyl ester (27) were isolated, together with sixteen known tannins and related compounds. The structures of these compounds were established on the basis of spectroscopic and chemical evidence.

  从芳香 Syzygium aromaticum MERR. et PERRY（桃金娘科）的干燥叶片中发现了十一种新化合物，即丁香酚 4-O-β-D-(6'-O-galloyl)glucopyranoside (17)、2-甲基-5, 7-二羟基色酮 8-C-β-D-glucopyranoside (18) 及其 6'-O-gallate (19)、2, 4, 6-三羟基苯乙酮 3-C-β-D-glucopyranoside (20) 及其 2'-O- (21)、6'-O- (22)、2'、(23)、2', 6'-di-O- (24)、2', 3', 6'-tri-O- (25)、2', 3', 4', 6'-tetra-O-gallate (26) 和 2',3'-di-O-galloyl-4',6'-O-(S)-hexahydroxydiphenoyl ester (27)。这些化合物的结构是根据光谱和化学证据确定的。