2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-1H-indole | 220915-57-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-1H-indole
• 英文别名: (1R)-1,5-anhydro-1-C-(2-indolyl)-2,3,4,6-tetra-O-benzyl-D-mannitol；2-[(2R,3R,4R,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]-1H-indole
• CAS: 220915-57-1
• 化学式: C₄₂H₄₁NO₅
• 分子量: 639.791
• InChiKey: KOWYLKDOLHMQFL-MHBOMZLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  48
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  61.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-1H-indole 在 palladium dihydroxide 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以74%的产率得到(2R,3S,4R,5S,6R)-2-Hydroxymethyl-6-(1H-indol-2-yl)-tetrahydro-pyran-3,4,5-triol
  参考文献：
  名称：

  α-C-Mannosyltryptophan is not recognized by conventional mannose-binding lectins

  摘要：

  alpha-C-Mannosyltryptophan (C-Man-Trp) is a novel, naturally occurring C-linked carbohydrate-protein linkage first found in 1994 from human ribonuclease 2. Since then, a number of C-Man-Trp residue have been found from several important proteins such as interleukin 12beta, components of complement system, thrombospondin-1, and erythropoietin receptor, however, the biological functions have remained unknown even though its biosynthetic pathway has been revealed. In order to find a clue as to the biological functions, we examined the affinity of C-Man-Trp with conventional mannose lectin such as concanavarin A (Con A) and mannose-binding lectin (MBL). The affinity of C-Man-Trp with Con A, a typical mannose-binding lectin from plant was examined using a Con A-Sepharose column. Unlike.p-nitrophenyl-alpha-O-Man, C-Man-Trp was not retained on the column. MBL-C, a major mannose-binding lectin purified from mouse serum, did not bind with N-biotinylated C-Man-Trp, judging from ELISA based assay. These results imply that C-Man-Trp may be recognized with the other specific proteins associated with its unknown biological functions. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.02.009
• 作为产物：
  描述：

  1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-mannopyranose 在 palladium diacetate copper(l) iodide 、 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.66h， 生成 2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-1H-indole
  参考文献：
  名称：

  Stereocontrolled syntheses of α-C-mannosyltryptophan and its analogues

  摘要：

  通过 10 个步骤（包括以下关键步骤：甘露糖衍生物与链烷乙炔的 C-糖苷化反应、卡斯特罗吲哚合成、Sc(ClO4)3 促进与 L-丝氨酸衍生的氮丙啶羧酸酯偶联）从市售的δ-甲基-D-甘露糖苷中完全合成了δ-C-甘露糖基色氨酸（C-Man-Trp），这是一种天然的 C-糖基氨基酸。C-Man-Trp 的葡萄糖和半乳糖类似物也是用类似方法合成的。本文简要讨论了合成的 C-糖基色氨酸及其合成中间体的构象分析。

  DOI：

  10.1039/b414905j

文献信息

• Compound 2-amino-3-[2-(&agr;-mannopyranosyl)indol-3-yl]propionic acid, process for preparing the same, and method for inspecting function of living body with the novel compound
  申请人：Kyowa Medex Co., Ltd.

  公开号：US06610502B1

  公开（公告）日：2003-08-26

  The present invention relates to a novel endogenous compound 2-amino-3-[2-(&agr;-mannopyranosyl)indole-3-yl]propionic acid; to a method for testing a biological function by quantitating 2-amino-3-[2-(&agr;-mannopyranosyl)indole-3-yl]propionic acid in a collected biological sample and determining the biological function based on the quantitated values; to an antibody specifically reactive with 2-amino-3-[2-(&agr;-mannopyranosyl)indole-3-yl]propionic acid; to a hybridoma that produces the antibody; to a method for immunologically quantitating 2-amino-3-[2-(&agr;-mannopyranosyl)indole-3-yl]propionic acid in a sample by using the antibody; and to a process for producing a 2-amino-3-[2-(&agr;-mannopyranosyl)indole-3-yl]propionic acid derivative.

  本发明涉及一种新的内源性化合物2-氨基-3-[2-(α-甘露糖苷基)吲哚-3-基]丙酸；一种通过定量收集的生物样品中的2-氨基-3-[2-(α-甘露糖苷基)吲哚-3-基]丙酸并根据定量值确定生物功能的测试生物功能的方法；一种特异性与2-氨基-3-[2-(α-甘露糖苷基)吲哚-3-基]丙酸反应的抗体；一种产生该抗体的杂交瘤；一种使用该抗体免疫学定量检测样品中的2-氨基-3-[2-(α-甘露糖苷基)吲哚-3-基]丙酸的方法；以及一种制备2-氨基-3-[2-(α-甘露糖苷基)吲哚-3-基]丙酸衍生物的方法。
• Palladium-Catalyzed Direct C–H Glycosylation of Free (<i>N</i>-H) Indole and Tryptophan by Norbornene-Mediated Regioselective C–H Activation
  作者：Neha Singh Chauhan、Atul Dubey、Pintu Kumar Mandal

  DOI：10.1021/acs.orglett.2c02537

  日期：2022.10.7

  We describe the palladium-catalyzed direct C–H glycosylation of free N-H indole or tryptophan for the stereoselective synthesis of 2-glycosylindoles and tryptophan-C-glycosides. This reaction relies on the ortho-directing transient mediator norbornene, which underwent regioselective C–H functionalization at the indole or tryptophan ring, providing high chemoselectivity. This method offers a more straightforward

  我们描述了钯催化的游离N -H吲哚或色氨酸的直接 C-H 糖基化，用于立体选择性合成 2-糖基吲哚和色氨酸-C-糖苷。该反应依赖于邻位定向瞬时介质降冰片烯，降冰片烯在吲哚或色氨酸环上经历区域选择性 C-H 功能化，提供高化学选择性。这种方法提供了一种更直接、步骤经济且具有成本效益的途径来构建C-糖苷。可以在 C3 和N -H处进一步功能化克级适用构建块，显示本方法的稳健性。
• NOVEL COMPOUND 2-AMINO-3-[2-(a)-MANNOPYRANOSYL)INDOL-3-YL]PROPIONIC ACID, PROCESS FOR PREPARING THE SAME, AND METHOD FOR INSPECTING FUNCTION OF LIVING BODY WITH THE NOVEL COMPOUND
  申请人：KYOWA MEDEX CO., LTD.

  公开号：EP1016866A1

  公开（公告）日：2000-07-05

  A novel in vivo compound 2-amino-3-[2-(α-mannopyranosyl)indol-3-yl]propionic acid; a method for inspecting the function of the living body, characterized by quantitatively determining 2-amino-3-[2-(α-mannopyranosyl)indol-3-yl]propionic acid in a harvested living body sample and judging the function of the living body from the determined value; an antibody which specifically reacts with 2-amino-3-[2-(α-mannopyranosyl)indol-3-yl]propionic acid; a hybridoma which produces the antibody; a method for immunologically assaying 2-amino-3-[2-(α-mannopyranosyl)indol-3-yl]propionic acid, characterized by immunologically assaying 2-amino-3-[2-(α-mannopyranosyl)indol-3-yl]propionic acid in a sample with the antibody; and a process for preparing 2-amino-3-[2-(α-mannopyranosyl)indol-3-yl]propionic acid derivatives.

  一种新型活体化合物 2-氨基-3-[2-(α-吡喃甘露糖基)吲哚-3-基]丙酸；一种检查活体功能的方法，其特征在于定量测定采集的活体样本中的 2-氨基-3-[2-(α-吡喃甘露糖基)吲哚-3-基]丙酸，并根据测定值判断活体的功能；与 2-氨基-3-[2-(α-吡喃甘露糖基)吲哚-3-基]丙酸特异性反应的抗体；一种产生该抗体的杂交瘤；一种对 2-氨基-3-[2-(α-吡喃甘露糖基)吲哚-3-基]丙酸进行免疫测定的方法，其特征在于用该抗体对样品中的 2-氨基-3-[2-(α-吡喃甘露糖基)吲哚-3-基]丙酸进行免疫测定；以及一种制备 2-氨基-3-[2-(α-吡喃甘露糖基)吲哚-3-基]丙酸衍生物的工艺。
• NOVEL COMPOUND 2-AMINO-3-[2-(ALPHA-MANNOPYRANOSYL) INDOL-3-YL] PROPIONIC ACID, PROCESS FOR PREPARING THE SAME, AND METHOD FOR INSPECTING FUNCTION OF LIVING BODY WITH THE NOVEL COMPOUND
  申请人：KYOWA MEDEX CO., LTD.

  公开号：EP1016866B1

  公开（公告）日：2006-10-25
• US6610502B1
  申请人：——

  公开号：US6610502B1

  公开（公告）日：2003-08-26