primeverose | 498-05-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: primeverose
• 英文别名: Primeverose; 6-O-β-D-Xylopyranosyl-D-glucose；6-O-(beta-D-xylopyranosyl)-D-glucopyranose；(3R,4S,5S,6R)-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxane-2,3,4,5-tetrol
• CAS: 498-05-5
• 化学式: C₁₁H₂₀O₁₀
• 分子量: 312.274
• InChiKey: QYNRIDLOTGRNML-XJBKZTKUSA-N

物化性质

• 沸点：
  724.6±60.0 °C(Predicted)
• 密度：
  1.65±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  169
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  primeverose 在 sodium aluminate 作用下， 以 水 为溶剂， 反应 4.5h， 以77%的产率得到6-O-(β-D-xylopyranosyl)-D-fructofuranose
  参考文献：
  名称：

  Versatile building blocks from disaccharides: glycosylated 5-hydroxymethylfurfurals

  摘要：

  A practical protocol for the elaboration of O-glycosyl-HMF's from glycosyl-(1 -> 6)-glucoses is reported, the two steps involving aluminate-promoted isomerization to the respective 6-O-glycosyl-fructoses and subsequent selective dehydration of the fructose portion. Accordingly, melibiose, gentiobiose, and primeverose are converted into the corresponding 2-uloses and, then, into alpha-GalMF 11, beta-GMF 12, and beta-XylMF 13. Pt/C-catalyzed oxidation with oxygen in NaOH at 25 degrees C efficiently generated the respective furoic acids from alpha-GalMF and alpha-GMF, whilst Pt/O-2 in water at 50 degrees C also oxidizes the primary OH to give the dicarboxylic acids 15 and 17-key building blocks for the generation of novel types of polyesters and polyamides. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.12.010
• 作为产物：
  描述：

  p-nitrophenyl 6-O-β-D-xylopyranosyl-β-D-glucopyranoside 在 β-primeverosidase 作用下， 以 various solvent(s) 为溶剂， 生成 primeverose
  参考文献：
  名称：

  Expression and Biochemical Characterization of β-Primeverosidase and Application of β-Primeverosylamidine to Affinity Purification

  摘要：

  β-Primeverosidase（PD）是一种家族1糖苷酶，催化β-早春花苷（6-O-β-d-木糖吡喃糖基-β-d-葡萄吡喃糖苷）水解，释放出早春花二糖。为了研究PD如何识别β-早春花苷的二糖部分，我们通过杆状病毒-昆虫细胞系统表达了重组PD。重组PD从High Five细胞中分泌出来，并进行了N-糖基化修饰和N端信号肽的正确切割。重组PD对β-早春花苷的糖苷部分表现出高度的底物特异性，与茶树中天然PD的底物特异性一致。接下来，合成了β-糖苷酰胺作为底物类似物抑制剂。β-早春花苷酰胺强烈抑制PD活性，而β-葡萄糖苷酰胺没有抑制作用。因此，β-早春花苷酰胺是一个理想的化学工具，用于探测PD活性位点中二糖的识别。使用β-早春花苷酰胺作为配体制备了PD的亲和吸附剂。亲和层析获得了高纯度的大量PD，允许进行晶体学研究。

  DOI：

  10.1271/bbb.70447

文献信息

• Enzymatic synthesis of β-xylosyl-oligosaccharides by transxylosylation using two β-xylosidases of glycoside hydrolase family 3 from Aspergillus nidulans FGSC A4
  作者：Adiphol Dilokpimol、Hiroyuki Nakai、Charlotte H. Gotfredsen、Maaike Appeldoorn、Martin J. Baumann、Natsuko Nakai、Henk A. Schols、Maher Abou Hachem、Birte Svensson

  DOI：10.1016/j.carres.2010.12.010

  日期：2011.2

  gave inferior yields on these acceptors. The regioselectivity was acceptor dependent and primarily involved beta-1,4 or 1,6 product linkage formation although minor products with different linkages were also obtained. Five of the 18 transxylosylation products obtained from D-lyxose, D-galactose, turanose and sucrose (two products) as acceptors were novel xylosyl-oligosaccharides, beta-D-Xylp-(1-->4)-D-Lyxp

  来自构巢曲霉FGSCA4，BxlA和BxlB的构巢曲霉糖苷水解酶家族3（GH 3）的两个β-木糖苷酶在巴斯德毕赤酵母中重组产生，并分别以16和118mg / L的产率分泌到培养上清液中。BxlA表现出比BxlB高约六倍的催化效率（k（cat）/ K（m））（对聚硝基苯基β-D-木吡喃糖苷（pNPX）和β-1,4-木糖寡糖（聚合度2-6）） 。对于这两种酶，k（cat）/ K（m）随着β-1,4-木糖寡糖链长的增加而降低。使用pNPX作为供体，以9种单糖，7种二糖和两种糖醇作为受体，通过反式木糖基化反应合成了18种不同的β-木糖基-低聚糖，收率为2-36％（BxlA）和6-66％（BxlB）。BxlA使用了单糖D-甘露糖，D-lyxose，D-talose，D-木糖，D-阿拉伯糖，L-岩藻糖，D-葡萄糖，D-半乳糖和D-果糖为受体，而BxlB使用相同的物质，除了D-糖，D-阿拉伯糖和L-岩藻
• Substrate Specificity of β-Primeverosidase, A Key Enzyme in Aroma Formation during Oolong Tea and Black Tea Manufacturing
  作者：Seung-Jin MA、Masaharu MIZUTANI、Jun HIRATAKE、Kentaro HAYASHI、Kensuke YAGI、Naoharu WATANABE、Kanzo SAKATA

  DOI：10.1271/bbb.65.2719

  日期：2001.1

  monoglycoside of 2-phenylethanol to investigate the substrate specificity of the purified beta-primeverosidase from fresh leaves of a tea cultivar (Camellia sinensis var. sinensis cv. Yabukita) in comparison with the apparent substrate specificity of the crude enzyme extract from tea leaves. The crude enzyme extract mainly showed beta-primeverosidase activity, although monoglycosidases activity was present

  我们合成了9种二糖苷和2-苯基乙醇单糖苷，以研究茶树种（Camellia sinensis var。sinensis cv。Yabukita）鲜叶中纯化的β-primeverosidase的底物特异性，并比较其表面底物特异性。茶叶中的粗酶提取物。粗酶提取物主要表现出β-primeverosidase活性，尽管在一定程度上存在单糖苷酶活性。纯化的β-primeverosidase对糖蛋白部分显示非常狭窄的底物特异性，尤其是对β-primeverosyl（6-O-β-D-吡喃吡喃糖基-β-D-葡萄糖基吡喃糖基）部分的特异性。这些酶会水解天然存在的二糖苷，例如β-primeveroside，β-vicianoside，β-acuminoside，β-龙胆苷和6-O-α-L-阿拉伯呋喃糖基-β-D-吡喃葡萄糖苷，但无法水解合成的非天然二糖苷。纯化的酶对2-苯乙基β-D-吡喃葡萄糖苷没有活性。该酶将
• Isolation and Characterization of a β-Primeverosidase-Like Enzyme from<i>Penicillium multicolor</i>
  作者：Kazutaka TSURUHAMI、Shigeharu MORI、Satoshi AMARUME、Shigetaka SARUWATARI、Takeomi MURATA、Jun HIRAKAKE、Kanzo SAKATA、Taichi USUI

  DOI：10.1271/bbb.70.691

  日期：2006.1

  p-Nitrophenyl and eugenyl β-primeveroside (6-O-β-D-xylopyranosyl-β-D-glucopyranoside) hydrolytic activity was found in culture filtrate from Penicillium multicolor IAM7153, and the enzyme was isolated. The enzyme was purified as a β-primeverosidase-like enzyme by precipitation with ammonium sulfate followed by successive chromatographies on Phenyl Sepharose, Mono Q, and β-galactosylamidine affinity columns. The molecular mass was estimated to be 50 kDa by SDS–PAGE and gel filtration. The purified enzyme was highly specific toward the substrate p-nitrophenyl β-primeveroside, which was cleaved in an endo-manner into primeverose and p-nitrophenol, but a series of β-primeveroside as aroma precursors were hydrolyzed only slightly as substrates for the enzyme. In analyses of its hydrolytic action and kinetics, the enzyme showed narrow substrate specificity with respect to the aglycon and glycon moieties of the diglycoside. We conclude that the present enzyme is a kind of β-diglycosidase rather than β-primeverosidase.

  从多彩青霉IAM7153的培养滤液中发现了对p-硝基苯基和丁香酚β-樱草糖苷（6-O-β-D-木糖吡喃糖基-β-D-葡萄吡喃糖苷）的水解活性，并分离出了该酶。该酶通过硫酸铵沉淀，然后依次通过苯基琼脂糖、Mono Q和β-半乳糖苷酰胺亲和柱层析纯化，类似于一种β-樱草糖苷酶。通过SDS-PAGE和凝胶过滤法估算其分子质量为50 kDa。纯化的酶对底物p-硝基苯基β-樱草糖苷具有高度特异性，以内切方式裂解为樱草糖和p-硝基苯酚，但对一系列作为香气前体的β-樱草糖苷底物的水解作用轻微。在其水解作用和动力学分析中，该酶对二糖苷的糖苷配基和糖基部分表现出较窄的底物特异性。我们得出结论，目前的酶是一种β-二糖苷酶，而不是β-樱草糖苷酶。
• Un nouvel heteroside nitré extrait d'Annona squamosa
  作者：P. Forgacs、J.F. Desconclois、J. Provost、R. Tiberghien、A. Touché

  DOI：10.1016/0031-9422(80)83102-5

  日期：1980.1

  Abstract A new glycoside was isolated from a 60% methanol extract of dried leaves and stems of Annona squamosa . Its chemical structure was determined as 4-(-2-nitroethyl)-1-[(6- O -β- d -xylopyranosyl-β- d -glucopyranosyl)oxy] benzene.

  摘要 从番荔枝干叶和茎的60%甲醇提取物中分离得到一种新苷。其化学结构确定为4-(-2-硝基乙基)-1-[(6-O-β-d-吡喃木糖基-β-d-吡喃葡萄糖基)氧基]苯。
• SEN, ASISH K.;BANERJI, NILIMA, INDIAN J. CHEM. B , 28,(1989) N0, C. 818-823
  作者：SEN, ASISH K.、BANERJI, NILIMA

  DOI：——

  日期：——