penta-O-acetyl-D-galactonic acid nitrile | 35439-42-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: penta-O-acetyl-D-galactonic acid nitrile
• 英文别名: galactose pentaacetate aldononitrile；per-O-acetyl-D-galactose aldonitrile；D-galactose aldonitrile peracetate；D-galactonitrile acetate；Penta-O-acetyl-D-galaktonsaeure-nitril；Pentaacetyl-d-galaktonsaeure-nitril；2,3,4,5,6-Penta-O-acetyl-D-galactononitrile；[(2R,3S,4R,5S)-2,3,4,5-tetraacetyloxy-5-cyanopentyl] acetate
• CAS: 35439-42-0
• 化学式: C₁₆H₂₁NO₁₀
• 分子量: 387.343
• InChiKey: INCBLRCTSZYSJE-JJXSEGSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  27
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  155
• 氢给体数：
  0
• 氢受体数：
  11

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  penta-O-acetyl-D-galactonic acid nitrile 在 氢溴酸 、 sodium methylate 、 溶剂黄146 作用下， 生成 D-galactonamide
  参考文献：
  名称：

  Zemplen et al., Chemische Berichte, 1938, vol. 71, p. 774

  摘要：

  DOI：
• 作为产物：
  描述：

  galactose oxime 在 乙酸酐 作用下， 以 吡啶 为溶剂， 反应 0.5h， 生成 penta-O-acetyl-D-galactonic acid nitrile
  参考文献：
  名称：

  Antioxidant activity of a water-soluble polysaccharide purified from Pteridium aquilinum

  摘要：

  A water-soluble crude polysaccharide, obtained from fern Pteridium aquilinum, was fractionated by DEAE-Sepharose Fast-Flow column chromatography, and purified by Sephacryl S-400 HR column chromatography. The average molecular weight (M-w) of the purified polysaccharide (PLP) is 458,000 Da. The monosaccharide components of PLP were characterized by gas chromatography (GC), and the majority of the monosaccharide components was glucose (relative mass 58.1%) with low levels of galactose, mannose, rhamnose, and arabinose (relative mass 18.7%, 6.8%, 10.2%, and 6.1%, respectively). The Fourier-transform infrared spectra (FTIR) of PLP revealed typical characteristics of polysaccharides. On the basis of the ferric-reducing antioxidant power assay (FRAP), DPPH radical-scavenging, the superoxide radical assay, and self-oxidation of 1,2,3-phentriol assay, the antioxidant activities of PLP were investigated. The purified polysaccharide was demonstrated to have strong reductive power (FRAP value: 827.6 mu mol/L), moderate scavenging activities against DPPH radicals (83.1%) and superoxide radicals (60.5%), and moderate inhibiting power for self-oxidation of 1,2,3-phentriol (52.4%). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.10.021

文献信息

• Acylic Sugar Derivatives for GC/MS Analysis of ¹³C-Enrichment during Carbohydrate Metabolism
  作者：Neil P. J. Price

  DOI：10.1021/ac049198m

  日期：2004.11.1

  localize and quantify the fractional incorporation of 13C isotope into each carbon atom of precursor-derived metabolites. In this paper, several carbohydrate derivatization procedures (peracetylation, deuterioalditol acetates, and aldononitrile acetates) are evaluated for the positional isotopic information obtained by gas chromatography/electron impact mass spectrometry (GC/EI-MS). These derivatives

  稳定同位素示踪剂与气相色谱/质谱法（GC / MS）结合进行代谢谱分析是一种用于测定代谢途径中底物再分布的成熟技术。该分析依赖于定位和定量将13 C同位素部分掺入前体衍生代谢物的每个碳原子中的能力。在本文中，针对通过气相色谱/电子轰击质谱（GC / EI-MS）获得的位置同位素信息，评估了几种碳水化合物的衍生化方法（过乙酰化，乙酸氘代醛糖醇和乙酸醛醇）。比较了这些衍生物，以定量评估13C标记的醛糖和酮糖的同位素异构体中13C的分布，以及15种己糖，戊糖，和生物来源的氨基糖已被评估。此外，已开发出一种用于GC / MS的新型碳水化合物衍生物（二烷基二硫代乙缩醛乙酸酯），可保留原始单糖的异头碳上的电荷。这些衍生物的电子碰撞电离会产生良好解析的碱基峰，该峰由C1-C2键断裂产生，电荷保留在C1硫醇基上。二烷基二硫缩醛乙酸酯特别适合于测量同位素富集到醛糖糖特征异头碳中，并将有助于对碳水化合物途径中
• Byproducts in the preparation of penta-O-acetyl-d-hexononitriles from d-galactose and d-glucose
  作者：Richard H. Furneaux

  DOI：10.1016/0008-6215(83)88240-8

  日期：1983.3

  is generally assumed. Instead, N -hydroxy- d -glycosylamine hexaacetates are formed as byproducts, in part by a kinetically controlled ring-closure of the sugar oxime, concomitant with acetylation. From preparative isolation of the products, d -galactose gave the nitrile (67%), and the β-furanose (16%), α-furanose (1%), and β-pyranose (2%) isomers of the cyclic hexaacetate, whereas d -glucose gave

  摘要制备用于glc分析的d-半乳糖和d-葡萄糖的过-O-乙酰化醛醇腈衍生物的常用方法包括肟的形成和乙酰化。但是，它们并不像通常认为的那样将腈作为唯一的产品。相反，N-羟基-d-糖基胺六乙酸盐是作为副产物形成的，部分是通过糖肟的动力学控制的闭环以及乙酰化而形成的。从产物的制备分离中，d-半乳糖得到了环六乙酸盐的腈（67％）和β-呋喃糖（16％），α-呋喃糖（1％）和β-吡喃糖（2％）异构体，而d-葡萄糖生成腈（63％），β-呋喃糖（14％）和β-吡喃糖（8％）异构体。
• Cyclopentadienyl–Ruthenium(II) and Iron(II) Organometallic Compounds with Carbohydrate Derivative Ligands as Good Colorectal Anticancer Agents
  作者：Pedro R. Florindo、Diane M. Pereira、Pedro M. Borralho、Cecília M. P. Rodrigues、M. F. M. Piedade、Ana C. Fernandes

  DOI：10.1021/acs.jmedchem.5b00403

  日期：2015.5.28

  ruthenium(II) and iron(II) organometallic compounds of general formula [(η5-C5H5)M(PP)Lc][PF6], bearing carbohydrate derivative ligands (Lc), were prepared and fully characterized and the crystal structures of five of those compounds were determined by X-ray diffraction studies. Cell viability of colon cancer HCT116 cell line was determined for a total of 23 organometallic compounds and SAR’s data analysis

  新钌（II）和铁（II）通式[（η的有机金属化合物5 -C 5 H ^ 5）M（PP）LC ] [PF 6 ]，轴承碳水化合物衍生物配位体（LC），制备并充分表征和通过X射线衍射研究确定了其中5种化合物的晶体结构。确定了总共23种有机金属化合物对结肠癌HCT116细胞系的细胞生存力，并且该库中的SAR数据分析表明，细胞毒性活性对碳水化合物部分，接头，膦大分子和金属中心具有有趣的依赖性。更重要的是，两种化合物14Ru和18Ru与奥沙利铂IC相匹配CC化疗中使用的标准金属药物50（0.45μM）和我们的领先化合物14Ru对HCT116细胞的细胞毒性比奥沙利铂明显更高，从而触发caspase-3和-7活性水平升高，并呈剂量依赖性方式。
• Determination of [13C]galactose enrichment in human plasma by gas chromatography/positive chemical ionization tandem mass spectrometry
  作者：P. Thomas Fenn、Cong Ning、Stanton Segal、Ian A. Blair

  DOI：10.1002/(sici)1096-9888(200002)35:2<218::aid-jms932>3.0.co;2-8

  日期：2000.2

  present in much higher concentrations. We have developed a method based on gas chromatography/positive chemical ionization tandem mass spectrometry (GC/PCI-MS/MS) for the precise and accurate determination of plasma [(13)C]galactose enrichment. The method employed a pentaacetylaldononitrile derivative of galactose in order to improve its GC and MS characteristics. Peak areas resulting from the transitions

  半乳糖血症是一种由于半乳糖-1-磷酸尿嘧啶转移酶的缺乏而导致的潜在致命疾病。为了进行旨在进一步阐明疾病病因的机制研究，我们需要一种方法来监测单次口服或静脉内注射[1-（13）C]半乳糖后血浆半乳糖中（13）C的富集。血浆[（13）C]半乳糖富集的测定需要具有极高特异性的方法，因为其他低分子量血浆成分和葡萄糖（一种存在于更高浓度的异构体）的潜在干扰。我们已经开发了一种基于气相色谱/正化学电离串联质谱（GC / PCI-MS / MS）的方法，用于精确和准确地测定血浆[（13）C]半乳糖富集。该方法使用了半乳糖的五乙酰基醛基腈衍生物，以改善其GC和MS特性。由转换m / z 328-> 106和m / z 329-> 107产生的峰面积用于量化标记和未标记半乳糖的相对丰度。该方法的验证是通过测定半乳糖浓度和（13）C富集范围内的精密度和准确性来进行的。在存在4 mM葡萄糖的情况下，GC / PCI-MS
• Benign Intracranial Hypertension Associated With Budesonide Treatment in Children With Crohn's Disease
  作者：Arie Levine、Nathan Watemberg、Hanoch Hager、Yoram Bujanover、Ami Ballin、Tally Lerman-Sagie

  DOI：10.1177/088307380101600617

  日期：2001.6

  Oral budesonide in adult studies is a potent corticosteroid with decreased systemic bioavailability and an improved adverse effect profile in comparison with prednisone. It has recently been introduced for the treatment of inflammatory bowel disease in Europe, Canada, and Israel. Benign intracranial hypertension has rarely been associated with corticosteroid therapy but has not been reported in association with budesonide therapy. Three adolescents with Crohn's disease and poor nutritional status developed benign intracranial hypertension while receiving oral budesonide. All three patients had previously received multiple courses of prednisone during the course of their disease, without developing intracranial hypertension. Benign intracranial hypertension resolved after medication withdrawal and did not recur with subsequent use of prednisone. Evaluation for benign intracranial hypertension should be considered in patients with inflammatory bowel disease who develop headache while receiving oral budesonide. This side effect may be associated with poor nutritional status. (J Child Neurol 2001;16:458-461).

  口服布地奈德在成人研究中是一种有效的皮质类固醇，其全身生物利用度降低且不良反应比泼尼松更好。最近，它已经在欧洲、加拿大和以色列用于治疗炎症性肠病。良性颅内高压症很少与皮质类固醇治疗有关，但尚未有报道与布地奈德治疗有关。三名患有克罗恩病和营养状况差的青少年在口服布地奈德期间发生了良性颅内高压症。这三名患者在疾病过程中先前接受了多次泼尼松治疗，但没有发生颅内高压症。停药后，良性颅内高压症得到缓解，并且在随后使用泼尼松时没有再次发生。在接受口服布地奈德治疗期间出现头痛的炎症性肠病患者应考虑进行良性颅内高压症评估。这种副作用可能与营养状况差有关。（《儿科神经学杂志》2001年；16：458-461）。