3,4,6-tri-O-acetyl-2-azidoacetamido-2-deoxy-D-galactopyranose | 653600-58-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-tri-O-acetyl-2-azidoacetamido-2-deoxy-D-galactopyranose
• 英文别名: (2R,3R,4R,5R)-2-(acetoxymethyl)-5-(2-azidoacetamido)-6-hydroxytetrahydro-2H-pyran-3,4-diyl diacetate；3,4,6-Tri-O-acetyl-N-azidoacetylgalactosamine；[(2R,3R,4R,5R)-3,4-diacetyloxy-5-[(2-azidoacetyl)amino]-6-hydroxyoxan-2-yl]methyl acetate
• CAS: 653600-58-9
• 化学式: C₁₄H₂₀N₄O₉
• 分子量: 388.334
• InChiKey: RESQIFNXKPQAHZ-GQYPCLOQSA-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：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  152
• 氢给体数：
  2
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-2-azidoacetamido-2-deoxy-D-galactopyranose 在 四氮唑 、 四(三苯基膦)钯 、 sodium 4-methylbenzenesulfinate 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 7.17h， 生成
  参考文献：
  名称：

  Probing Glycosyltransferase Activities with the Staudinger Ligation

  摘要：

  The development of rapid screening methods for probing glycosyltransferase activities is essential for advancing the field of glycobiology. While assays for specific glycosyltransferases exist, there is no generalizable method that can be applied across the enzyme superfamily. Herein we describe a novel glycosyltransferase assay that exploits their unnatural substrate tolerance and the unique chemical reactivity of the azide. We applied this "azido-ELISA" to the family of polypeptide alpha-N-acetylgalactosaminyltransferases (ppGalNAcTs), all of which were able to transfer N-azidoacetylgalactosamine (GalNAz) from the unnatural nucleotide sugar donor UDP-GalNAz. The azide was detected and quantified by Staudinger ligation with a phosphine probe in a microtiter plate format. This approach should be applicable to any glycosyltransferase or group-transfer enzyme that tolerates unnatural azido substrates.

  DOI：

  10.1021/ja037692m
• 作为产物：
  描述：

  D-(+)-galactosamine hydrochloride 在 4-二甲氨基吡啶 、 乙酸肼 、 1-丙基磷酸酐 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 3,4,6-tri-O-acetyl-2-azidoacetamido-2-deoxy-D-galactopyranose
  参考文献：
  名称：

  A chemoenzymatic approach toward the preparation of site-specific antibody–drug conjugates

  摘要：

  An efficient chemical synthesis of UDP-N-azidoacetylgalactosamine (UDP-GalNAz) is presented, while the value of this molecule was demonstrated through its attachment to an antibody Fc domain. Thus, the antibody was first degalactosylated, which was followed by loading of the UDP-GalNAz with a recombinant galactosyltransferase. This engineered Azide-Fc-N-glycan antibody was subsequently 'clicked' by a strain-promoted alkyne-azide cycloaddition reaction for site-specific attachment of a fluorescent probe. The principles detailed will allow for the facile preparation of chemically defined homogeneous antibody-drug conjugates (ADCs). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.12.025

文献信息

• LABELING AND DETECTION OF POST TRANSLATIONALLY MODIFIED PROTEINS
  申请人：AGNEW Brian

  公开号：US20120301894A1

  公开（公告）日：2012-11-29

  Provided in certain embodiments are new methods for forming azido modified biomolecule conjugates of reporter molecules, carrier molecules or solid support. In other embodiments are provided methods for enzymatically labeling a biomolecules with an azide group.

  在某些实施例中，提供了形成带有报告分子、载体分子或固体支持物的偶联物的新方法，其中这些分子已经被进行了偶联修饰。在其他实施例中，提供了将生物分子以酰胺基团进行酶标记的方法。
• [EN] METHODS FOR PREPARING ANTIBODIES WITH A DEFINED GLYCOSYLATION PATTERN<br/>[FR] PROCÉDÉ DE PRÉPARATION D'ANTICORPS AYANT UN PROFIL DE GLYCOSYLATION DÉFINI
  申请人：MEDIMMUNE LLC

  公开号：WO2017132298A8

  公开（公告）日：2018-07-12