5-azido-5-deoxy-D-arabinofuranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-azido-5-deoxy-D-arabinofuranose
• 英文别名: 5-Azido-5-deoxy-D-arabinofuranose；(3S,4S,5R)-5-(azidomethyl)oxolane-2,3,4-triol
• 化学式: C₅H₉N₃O₄
• 分子量: 175.144
• InChiKey: FPNYNARZVKFPAC-ZRMNMSDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  84.3
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-azido-5-deoxy-D-arabinofuranose 在 sodium tetrahydroborate 、 sodium hydride 、 溶剂黄146 作用下， 以 吡啶 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 56.0h， 生成 5-azido-2,3,4-tri-O-benzyl-5-deoxy-D-arabinitol
  参考文献：
  名称：

  Synthesis of ethyl 2-acetamido-6-S-(5-amino-5-deoxy-β-d-arabinopyranosyl)-2-deoxy-1,6-dithio-β-d-glucopyranoside: a sulfur-linked 5-amino-5-deoxyglycopyranosyl disaccharide

  摘要：

  A novel pseudo-disaccharide having an imino sugar residue at the non-reducing end, namely, a sulfur-linked 5-amino-5-deoxyglycopyranosyl disaccharide, which is a potential specific inhibitor for glycosidases that recognize not only the glycosidic linkage but also the aglycone moiety, was synthesized. Glycosidation of N-Boc-5-amino-5-deoxy-D-arabinose with ethyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-1,6-dithio-beta-D- glucopyranoside in the presence of TsOH gave exclusively the corresponding 1,2-cis-linked thioglycoside. The interglycosidic linkage proved stable enough under conditions for the deprotection of the N-Boc group with TFA. This pseudodisaccharide was unstable at pH > 5, but stable at lower pH. The sulfur-linked 5-amino-5-deoxyglycopyranosyl disaccharide was shown to be formed from 5-amino-5-deoxy-D-arabinose and ethyl 2-acetamido-2-deoxy-1,6-dithio-beta-D-glucopyranoside in an acidic buffer solution.

  DOI：

  10.1016/s0008-6215(99)00253-0
• 作为产物：
  描述：

  1,2,3-tri-O-acetyl-5-hydroxy-D-arabinofuranose 在 sodium azide 、 sodium methylate 作用下， 以 吡啶 、 甲醇 、 二甲基亚砜 为溶剂， 反应 29.33h， 生成 5-azido-5-deoxy-D-arabinofuranose
  参考文献：
  名称：

  Synthesis of ethyl 2-acetamido-6-S-(5-amino-5-deoxy-β-d-arabinopyranosyl)-2-deoxy-1,6-dithio-β-d-glucopyranoside: a sulfur-linked 5-amino-5-deoxyglycopyranosyl disaccharide

  摘要：

  A novel pseudo-disaccharide having an imino sugar residue at the non-reducing end, namely, a sulfur-linked 5-amino-5-deoxyglycopyranosyl disaccharide, which is a potential specific inhibitor for glycosidases that recognize not only the glycosidic linkage but also the aglycone moiety, was synthesized. Glycosidation of N-Boc-5-amino-5-deoxy-D-arabinose with ethyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-1,6-dithio-beta-D- glucopyranoside in the presence of TsOH gave exclusively the corresponding 1,2-cis-linked thioglycoside. The interglycosidic linkage proved stable enough under conditions for the deprotection of the N-Boc group with TFA. This pseudodisaccharide was unstable at pH > 5, but stable at lower pH. The sulfur-linked 5-amino-5-deoxyglycopyranosyl disaccharide was shown to be formed from 5-amino-5-deoxy-D-arabinose and ethyl 2-acetamido-2-deoxy-1,6-dithio-beta-D-glucopyranoside in an acidic buffer solution.

  DOI：

  10.1016/s0008-6215(99)00253-0

文献信息

• Expanding the Scope of Metabolic Glycan Labeling in<i>Arabidopsis thaliana</i>
  作者：Yuntao Zhu、Xing Chen

  DOI：10.1002/cbic.201700069

  日期：2017.7.4

  root glycans in Arabidopsis thaliana. Nineteen monosaccharide analogues containing a bioorthogonal group (azide, alkyne, or cyclopropene) were synthesized and evaluated for metabolic incorporation into root glycans. Among these unnatural sugars, 14 (including three new compounds) were evaluated in plants for the first time. Our results showed that five unnatural sugars metabolically labeled root glycans

  代谢聚糖标记（MGL）已获得广泛的应用，并已成为探测生命系统糖基化的有用工具。在过去的三十年中，MGL的开发和应用主要集中在动物糖基化上。近来，利用MGL研究植物糖基化已引起人们的兴趣。在这里，我们描述了拟南芥根聚糖的荧光成像的MGL的系统评价。合成了十九个含有生物正交基团（叠氮化物，炔烃或环丙烯）的单糖类似物，并评估了其代谢是否掺入到根聚糖中。在这些非天然糖中，首次在植物中评估了14种（包括三种新化合物）。我们的结果表明，五种非天然糖可以有效地代谢标记根聚糖，并通过与荧光团的生物正交缀合使荧光成像成为可能。我们优化了拟南芥中MGL的实验程序。最后，沿着根部发育区观察到新合成的聚糖的独特分布模式，从而表明在根部发育过程中聚糖的生物合成受到调节。我们设想MGL将在植物糖生物学中找到广泛的应用。
• A Simple Synthesis of C-8 Modified 2-Keto-3-deoxy-d-manno-octulosonic Acid (KDO) Derivatives
  作者：Milton Kiefel、Renee Winzar、Jessica Philips

  DOI：10.1055/s-0029-1219356

  日期：2010.3

  This paper describes a simple and efficient method with which to prepare C-8 modified 2-keto-3-deoxy-d-manno-octulosonic acid (KDO) derivatives from C-5 modified arabinose derivatives.

  本文描述了一种简单高效的方法，可以从C-5修饰的阿拉伯糖衍生物制备C-8修饰的2-酮-3-脱氧-d-甘露-壬酸（KDO）衍生物。
• Synthesis of 1,5-dideoxy-1,5-imino-d-arabinitol (5-nor-l-fuco-1-deoxynojirimycin) and its application for the affinity purification and characterisation of α-l-fucosidase
  作者：Günter Legler、Arnold E. Stütz、Hermann Immich

  DOI：10.1016/0008-6215(95)00032-o

  日期：1995.7

  Abstract The title, 1,5-dideoxy-1,5-imino- d -arabinitol (2), was synthesized in seven steps from d - arabinose with 5-azido-5-deoxy- d -arabinofuranose as key intermediate and 40% overall yield. An affinity procedure employing the N-carboxypentyl derivative of 2 linked to aminohexyl agarose permitted the isolation of pure α- l - fucosidase from bovine kidney homogenate in two steps. Inhibition constants

  摘要以d-阿拉伯糖为主要原料，以5-叠氮基5-deoxy-d-阿拉伯呋喃糖为原料，经7个步骤合成了1,5-dideoxy-1,5-imino-d-arabinitol（2）。总产量。利用连接到氨基己基琼脂糖上的2的N-羧基戊基衍生物的亲和程序，可以分两步从牛肾脏匀浆中分离出纯的α-1-岩藻糖苷酶。纯化酶的抑制常数2为39μM（pH 5.0）至3μM（pH 7.0），在这些pH值下，对fuco -1-脱氧野oji霉素（1）的抑制作用约为KI的1,500倍。d-甘露聚糖和l-gulo-1-脱氧野oji霉素的K1值也表明了甲基1对抑制作用的较大贡献。1，2对K1的pH依赖性 和其他基本类似物与1-岩藻糖的K1非常相似（pH 5.0时为205μM，pH 7.0时为25μM）。另一方面，对硝基苯基α-1-岩藻糖苷的KM和对于甲基α-1-岩藻糖苷的K1随pH的变化很小。相对于不同的pH依赖性，相对于甲
• Synthesis of New N-Containing Maltooligosaccharides, .ALPHA.-Amylase Inhibitors, and Their Biological Activities.
  作者：Riichiro UCHIDA、Ayako NASU、Shoichi TOKUTAKE、Kouichi KASAI、Koichiro TOBE、Nobuyuki YAMAJI

  DOI：10.1248/cpb.47.187

  日期：——

  Fifteen new N-containing maltooligosaccharides were obtained using the chemoenzymatic method. Among these compounds, maltooligosaccharides having 6-amino-6-deoxy-D-sorbitol residue, (3R, 4R, 5R, 6S)-hexahydro-3, 4, 5, 6-tetrahydroxy-1H-azepine residue, and (3R, 5R)-3, 4, 5-trihydroxypiperidine residue at the reducing end showed strong inhibitory activities for human pancreatic α-amylase (HPA) (EC 3.2.1.1) and human salivary α-amylase (HSA). The administration of (3R, 4R, 5R, 6S)-hexahydro-3, 5, 6-trihydroxy-1H-azepine-4-yl O-α-D-glucopyranosyl-(1→4)-α-D-glucopyranoside (13, IC50=4.3×10-5M for HPA, IC50=8.2×10-5M for HSA) and (3R, 5R)-3, 5-dihydroxypiperidine-4-yl O-α-D-glucopyranosyl-(1→4)-α-D-glucopyranoside (18, IC50=3.4×10-5M for HPA, IC50=4.6×10-5M for HSA) to ICR mice suppressed postprandial hyperglycemia.

  利用化学酶法获得了 15 种新的含 N 的麦芽寡糖。在这些化合物中，还原端具有 6-氨基-6-脱氧-D-山梨醇残基、(3R, 4R, 5R, 6S)-hexahydro-3, 4, 5, 6-tetrahydroxy-1H-azepine 残基和 (3R, 5R)-3, 4, 5-trihydroxypiperidine 残基的麦芽寡糖对人胰腺α-淀粉酶（HPA）（EC 3.2.1.1）和人唾液α-淀粉酶（HSA）有很强的抑制活性。服用(3R, 4R, 5R, 6S)-六氢-3, 5, 6-三羟基-1H-氮杂卓-4-基 O-α-D-吡喃葡萄糖苷-(1→4)-α-D-吡喃葡萄糖苷（13，对 HPA 的 IC50=4.3×10-5M, 对 HSA 的 IC50=8.2×10-5M for HSA）和 (3R，5R)-3，5-二羟基哌啶-4-基 O-α-D-吡喃葡萄糖基-(1→4)-α-D-吡喃葡萄糖苷（18，IC50=3.4×10-5M for HPA，IC50=4.6×10-5M for HSA）给 ICR 小鼠服用可抑制餐后高血糖。
• Synthesis of 5-Amino-5-deoxypentonolactams
  作者：Karel Kefurt、Zdeňka Kefurtová、Věra Marková、Karla Slívová

  DOI：10.1135/cccc19961027

  日期：——

  5-Azido-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose (4) and 5-azido-5-deoxy-1,2-O-isopropylidene-β-D-arabinofuranose (10) were prepared starting from D-xylose and D-arabinose, respectively. Using the oxidation-reduction way for the C-3 epimerization, 5-azido-5-deoxy-1,2-O-isopropylidene-α-D-ribofuranose (15) and 5-azido-5-deoxy-1,2-O-isopropylidene-β-D-lyxofuranose (17) were obtained from 4 and 10, respectively. The derivatives 4, 10, 15 and 17 afforded by acid hydrolysis, oxidation with bromine and catalytic hydrogenation successively the corresponding 5-azido-5-deoxy-D-pentofuranoses 6, 11, 18, 19, 5-azido-5-deoxy-D-pentonolactones 7, 12, 20, 21 and 5-amino-5-deoxy-D-pentonolactams 8, 13, 22, 23.

  从D-木糖和D-阿拉伯糖开始制备5-Azido-5-deoxy-1,2-O-异丙基亚-α-D-木糖呋喃糖（4）和5-azido-5-deoxy-1,2-O-异丙基亚-β-D-阿拉伯呋喃糖（10）。使用氧化还原法进行C-3异构化，从4和10分别得到5-azido-5-deoxy-1,2-O-异丙基亚-α-D-核糖呋喃糖（15）和5-azido-5-deoxy-1,2-O-异丙基亚-β-D-莱克索呋喃糖（17）。通过酸水解、溴氧化和催化氢化，分别得到相应的5-azido-5-deoxy-D-戊糖呋喃糖6、11、18、19，5-azido-5-deoxy-D-戊内酯7、12、20、21和5-氨基-5-deoxy-D-戊内酰胺8、13、22、23。