D-glucuronamide | 3318-57-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: D-glucuronamide
• 英文别名: glucopyranosiduronamide；D-Glucuronsaeureamid；D-Glucuronamid；D-Gluconamid；Glucuronamid；Glucopyranuronamide；(2S,3S,4S,5R)-3,4,5,6-tetrahydroxyoxane-2-carboxamide
• CAS: 3318-57-8
• 化学式: C₆H₁₁NO₆
• 分子量: 193.156
• InChiKey: VOIFKEWOFUNPBN-AQKNRBDQSA-N

物化性质

• 沸点：
  545.7±50.0 °C(Predicted)
• 密度：
  1.859±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  133
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  D-glucuronamide 、 蔗糖 在 β-fructofuranosidase from Arthrobacter sp. K-1 、 β-fructofuranosidase from saccharomyces bisporus 作用下， 以 aq. phosphate buffer 为溶剂， 生成 β-D-fructofuranosyl-[2↔1]-6-amido-6-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Chemoenzymatic synthesis and properties of sucuronamide

  摘要：

  Using D-glucurono-6,3-lactone (GlcL) as a starting material, sucuronamide (SucAm) was synthesized in two steps using a chemoenzymatic method. In the first chemical synthesis, D-glucuronamide (GlcAm) was synthesized by treating GlcL with NH3 in ethanol. In the second enzymatic synthesis exploiting transfructosylation activity of -fructofuranosidase, which is inhibited by D-glucose, from Arthrobacter sp. K-1, addition of the sucrose non-assimilating yeast, Saccharomyces bisporus NBRC1131, to the reaction mixture increased SucAm production from GlcAm and sucrose. The overall molar yield of this disaccharide after purification by column chromatography and crystallization was 34.7%.

  DOI：

  10.1080/07328303.2017.1333122
• 作为产物：
  描述：

  葡醛内酯 在 氨 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以79.6%的产率得到D-glucuronamide
  参考文献：
  名称：

  Chemoenzymatic synthesis and properties of sucuronamide

  摘要：

  Using D-glucurono-6,3-lactone (GlcL) as a starting material, sucuronamide (SucAm) was synthesized in two steps using a chemoenzymatic method. In the first chemical synthesis, D-glucuronamide (GlcAm) was synthesized by treating GlcL with NH3 in ethanol. In the second enzymatic synthesis exploiting transfructosylation activity of -fructofuranosidase, which is inhibited by D-glucose, from Arthrobacter sp. K-1, addition of the sucrose non-assimilating yeast, Saccharomyces bisporus NBRC1131, to the reaction mixture increased SucAm production from GlcAm and sucrose. The overall molar yield of this disaccharide after purification by column chromatography and crystallization was 34.7%.

  DOI：

  10.1080/07328303.2017.1333122

文献信息

• Synthesis and biological evaluation of analogues of M6G
  作者：Claire Trécant、Alain Dlubala、Pascal George、Philippe Pichat、Isabelle Ripoche、Yves Troin

  DOI：10.1016/j.ejmech.2011.05.076

  日期：2011.9

  Synthesis and biological evaluation of new derivatives of Morphine-6-Glucuronide (M6G) are described. M6G is an active metabolite of morphine which displays more analgesia than morphine with a superior side effect profile but with a less efficiently BBB penetration. These phenomena could be explained by the presence of the glucuronide moiety, which confers a higher hydrophilic character compare to

  描述了吗啡-6-葡糖醛酸（M6G）的新衍生物的合成和生物学评估。M6G是吗啡的活性代谢产物，与吗啡相比，具有更高的镇痛效果，但副作用更强，但BBB的渗透效率较低。这些现象可以用葡糖醛酸苷部分的存在来解释，葡糖醛酸苷部分与吗啡相比具有更高的亲水性。在这种情况下，我们制备了三个M6G类似物，它们具有四唑，恶二唑和三唑并嘧啶部分，而不是糖的5位羧酸功能。这三种类似物甚至通过口服显示出比吗啡和M6G更高的镇痛特性。
• DERIVATIVES OF MORPHINE-6-GLUCURONIDE, PREPARATION METHOD THEREOF AND USE OF SAME IN THERAPEUTICS
  申请人：DLUBALA Alain

  公开号：US20110301107A1

  公开（公告）日：2011-12-08

  The disclosure relates to derivatives of morphine-6-glucuronide of formula (I) wherein R1 is as defined in the disclosure, or an acid addition salt thereof, as well as in hydrate or solvate form. The disclosure also relates to the preparation method thereof and to the use of same in therapeutics.

  该披露涉及公式(I)的吗啡-6-葡糖醇衍生物，其中R1如披露中定义，或其酸盐加合物，以及水合物或溶剂合物形式。该披露还涉及其制备方法以及在治疗中使用的相关内容。
• MOENOMYCIN ANALOGS, METHODS OF SYNTHESIS, AND USES THEREOF
  申请人：Kahne Daniel

  公开号：US20110136759A1

  公开（公告）日：2011-06-09

  The present invention provides novel moenomycin analogs as well as pharmaceutical compositions thereof, methods of synthesis, and methods of use in treating an infection by administering an inventive compound to a subject in need thereof. The moenomycin analogs may be prepared synthetically, biosynthetically, or semi-synthetically. The analogs are particularly useful in treating or preventing infections caused by Gram-positive organisms. Certain inventive compounds may have a broader spectrum of coverage, which includes Gram-negative organisms.

  本发明提供了新型的莫诺霉素类似物及其制药组合物，合成方法以及将创新化合物用于治疗感染的方法，通过将创新化合物给予需要治疗的受试者来治疗感染。莫诺霉素类似物可以通过化学合成，生物合成或半合成的方式制备。这些类似物在治疗或预防由革兰氏阳性菌引起的感染中特别有用。某些创新化合物可能具有更广泛的覆盖范围，包括革兰氏阴性菌。
• [EN] A COMBINATORIAL LIBRARY OF MOENOMYCIN ANALOGS AND METHODS OF PRODUCING SAME<br/>[FR] BIBLIOTHEQUE DE COMBINAISONS D'ANALOGUES DE MOENOMYCINE ET PROCEDES DE PRODUCTION DE CES ANALOGUES
  申请人：INCARA PHARMACEUTICAL CORP.

  公开号：WO1999026956A1

  公开（公告）日：1999-06-03

  (EN) A combinatorial chemical library of compounds structurally related to the moenomycin class of antibiotics has formula (I) wherein D is a donor mono- or disaccharide, A is an acceptor monosaccharide, and P-R is a lipophosphoglycerate mimetic group. Members of the library have a glycosidic linkage between the anomeric carbon of D and the C2 carbon of A, and the D-A moiety is in turn covalently linked through the anomeric carbon of A to the P-R group. Members of the library exhibit their greatest structural diversity in terms of substitutions occurring at the C3 position of the A residue, substitutions at the C2 position of the D residue, and different P-R groups used in assembling the compounds. Members of the library are preferably synthesized by solid phase techniques involving stepwise coupling of the respective units to a support, functionalizing the A and/or D saccharides either before or after immobilizing them on the support, and cleaving the assembled compounds from the support. Preferred functionalities attached to the sugar residues are amides, carbamates, ureas, sulfonamides, substituted amines, esters, carbonates, and sulfates. Exemplary P-R groups are derivatives of homoserine, glyceric acid, salicylates and mandelic acid. Members of the library can be screened for anti-microbial activity by contacting them with a culture of microbes and monitoring the growth rate of the microbes.(FR) L'invention concerne une bibliothèque chimique de combinaisons de composés apparentés par leur structure à la classe moénomycine des antibiotiques. Cette bibliothèque présente la formule (I), où D est un mono- ou disaccharide donneur, A est un monosaccharide accepteur, et P-R est un groupe mimétique de lipophosphoglycérate. Les éléments de la bibliothèque présentent une liaison glycosidique entre le carbone anomère de D et le carbone C2 de A, et la fraction D-A est à son tour liée par covalence par le carbone anomère de A au groupe P-R. Les éléments de la bibliothèque présentent leur plus grande diversité structurelle en termes de substitution au niveau de la position C3 du résidu A, des substitutions au niveau de la position C2 du résidu D, et différents groupes P-R utilisés pour assembler les composés. Les éléments de la bibliothèque sont, de préférence, synthétisés par des techniques en phase solide consistant à coupler, par étape, des unités correspondantes à un support, à fonctionnaliser des saccharides A et/ou D avant ou après les avoir immobilisés sur le support, et à scinder les composés assemblés du support. Les fonctionnalités préférées fixées aux résidus de sucre sont des amides, des carbamates, des urées, des sulfonamides, des amines substituées, des esters, des carbonates et des sulfates. Des groupes P-R donnés à titre d'exemple sont dérivés de l'homosérine, de l'acide glycérique, des salicylates et de l'acide mandélique. Les éléments de la bibliothèque peuvent être analysés afin de détecter l'activité anti-microbienne en les plaçant au contact d'une culture de microbes et en contrôlant le taux de croissance des microbes.

  该组合化学库包含结构上与莫烯霉素类抗生素相关的化合物，其通式为(I)，其中D是供体单或双糖，A是受体单糖，P-R是一个脂基磷酰甘油酸模拟基团。这些化合物在A残基的C3位上的取代、D残基的C2位上的取代以及用于组装化合物的不同P-R基团上表现出最大的结构多样性。该化学库优选通过固相技术合成，涉及逐步将相应的单元连接到支持物上，在固定于支持物之前或之后对A和/或D糖进行功能化，并从支持物上裂解组装的化合物。糖残基上的优选官能团包括酰胺、 carbamates（ Carbamate）、尿素、磺酰胺、取代胺、酯、碳酸盐和硫酸盐。示例性的P-R基团包括homoserine、glyceric acid、salicylates和mandelic acid等衍生物。该化学库可通过将其与微生物培养物接触，并监测微生物的生长速率来筛选其抗菌活性。
• A COMBINATORIAL LIBRARY OF MOENOMYCIN ANALOGS AND METHODS OF PRODUCING SAME
  申请人：Incara Pharmaceutical Corp.

  公开号：EP1047703A1

  公开（公告）日：2000-11-02