2-acetamido-2,6-dideoxymannose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-2,6-dideoxymannose
• 英文别名: N-[(2S,3R,4R,5R)-3,4,5-trihydroxy-1-oxohexan-2-yl]acetamide
• 化学式: C₈H₁₅NO₅
• 分子量: 205.211
• InChiKey: CZRYIXLKTDHMMY-XVFCMESISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-acetamido-3,5,9-trideoxy-D-glycero-D-galacto-2-nonulopyranosonic acid 在 L-lactate dehydrogenase 、 NauAc aldolase 、 还原型辅酶Ⅰ 作用下， 以 水 为溶剂， 生成 丙酮酸 、 2-acetamido-2,6-dideoxymannose
  参考文献：
  名称：

  一种在完整糖蛋白上精确化学酶合成 13C 标记的唾液酸寡糖的方法：一种新的单锅 [3-13C]-标记唾液酸类似物的方法，通过控制可逆醛缩酶反应，酶促合成 [3-13C]糖蛋白上的-NeuAc-α-(2→3)-[U-13C]-Gal-β-(1→4)-GlcNAc-β-序列及其构象分析

  摘要：

  A one-pot enzymatic C-13-labeling method for the 3-position of sialic acid (NeuAc) analogues has been developed using NeuAc aldolase, lactate dehydrogenase (LDH), alcohol dehydrogenase (ADI-T), and nucleotide pyrophosphatase (NPP). This method consists of two steps, the first of which is degradation to 2-acetamido-2-deoxy-D-mannose (ManNAc) analogues. This degradation reaction was accelerated by a cofactor regeneration system which converts pyruvic acid into lactic acid using LDH, ADH, and beta-nicotinamide adenine dinucleotide oxidized form (beta-NAD(+)). The second step is condensation of the ManNAc analogue with [3-C-13]-pyruvic acid newly added after decomposition of the cofactor by nucleotide pyrophosphatase which play a role like switch to stop conversion of pyruvic acid into lactic acid. Five different NeuAc analogues have been labeled in good yields using this newly developed one-pot enzymatic procedure. Following conversion of [3-C-13]-NeuAc to CMP-[3-C-13]-NeuAc, enzymatic synthesis of [3-C-13]-NeuAc-alpha-(2-->3)-[U-C-13]-Gal-beta-(1-->4)-GlcNAc-beta-x-ovalbumin (x: hybrid type oligosaccharide) 23 and [3-C-13]-NeuAc-alpha-(2-->3)-[U-C-13]-Gal-beta-(1-->4)-GlcNAc-beta-OMe 26 (sialyl LacNAc) was performed using bovine beta-1,4-galactosyltransferase and rat recombinant alpha-2,3-sialyltransferase. The H-1 chemical shifts of all protons in [3-C-13]-NeuAc-alpha-(2-->3)-[U-C-13]-Gal-beta- on a glycoprotein were assigned by 2D HMQC, 1D HSQC-TOCSY, and the herein described 1D and 2D HSQC-TOCSY-NOESY-TOCSY method. More specifically, the 7-, 8-, and 9-protons of NeuAc could be observed by this HSQC-TOCSY-NOESY-TOCSY method even with only a single C-13 atom at the 3-position. In addition, 1D and 2D HMQC-NOESY spectra as well as carbon spin-lattice relaxation times (T-1) were measured to compare the conformational properties and dynamic behavior of the sialylgalactoside as part of the sialyl LacNAc 26 and when bound to a glycoprotein 23. These analyses suggested that the conformational properties of sialyl LacNAc are similar for both the conjugated and unconjugated forms, and that the torsional angle of the sialyl linkage, i.e., COOH-C2(NeuAc)-O-C3(Gal), is biased toward the anti (-146.7 degrees) conformation. In addition, the flexibility of galactosyl ring when bound to a glycoprotein appears to be significantly restricted by the attachment of NeuAc as compared with unconjugated sialyl LacNAc.

  DOI：

  10.1021/ja994211j

文献信息

• Probe compound for detecting and isolating enzymes and means and methods using the same
  申请人：Helmholtz-Zentrum für Infektionsforschung GmbH

  公开号：EP2230312A1

  公开（公告）日：2010-09-22

  The present invention relates to a probe compound that can comprise any substrate or metabolite of an enzymatic reaction in addition to an indicator component, such as, for example, a fluorescence dye, or the like. Moreover, the present invention relates to means for detecting enzymes in form of an array, which comprises any number of probe compounds of the invention which each comprise a different metabolite of interconnected metabolites representing the central pathways in all forms of life. Moreover, the present invention relates to a method for detecting enzymes involving the application of cell extracts or the like to the array of the invention which leads to reproducible enzymatic reactions with the substrates. These specific enzymatic reactions trigger the indicator (e.g. a fluorescence signal) and bind the enzymes to the respective cognate substrates. Moreover, the invention relates to means for isolating enzymes in form of nanoparticles coated with the probe compound of the invention. The immobilisation of the cognate substrates or metabolites on the surface of nanoparticles by means of the probe compounds allows capturing and isolating the respective enzyme, e.g. for subsequent sequencing.

  本发明涉及一种探针化合物，它可以包括酶反应的任何底物或代谢物，此外还包括指示成分，例如荧光染料或类似物。此外，本发明还涉及以阵列形式检测酶的方法，该阵列由任意数量的本发明探针化合物组成，每种探针化合物由代表所有生命形式中中心途径的相互关联的代谢物中的不同代谢物组成。此外，本发明还涉及一种检测酶的方法，该方法涉及将细胞提取物或类似物应用于本发明的阵列，从而导致与底物发生可重复的酶反应。这些特定的酶反应会触发指示剂（如荧光信号），并将酶与各自的同源底物结合。此外，本发明还涉及以涂覆有本发明探针化合物的纳米颗粒形式分离酶的方法。通过探针化合物将同源底物或代谢物固定在纳米颗粒表面，可以捕获和分离相应的酶，例如用于后续测序。
• Method for rapid in vitro synthesis of glycoproteins via recombinant production of N-glycosylated proteins in prokaryotic cell lysates
  申请人：Northwestern University

  公开号：US10829795B2

  公开（公告）日：2020-11-10

  Disclosed are methods, systems, components, and compositions for cell-free synthesis of glycosylated proteins. The glycosylated proteins may be utilized in vaccines, including anti-bacterial vaccines. The glycosylated proteins may include a bacterial polysaccharide conjugated to a carrier, which may be utilized to generate an immune response in an immunized host against the polysaccharide conjugated to the carrier. The glycosylated proteins may be synthesized in cell-free glycoprotein synthesis (CFGpS) systems using prokaryote cell lysates that are enriched in components for glycoprotein synthesis such as oligosaccharyltransferases (OSTs) and lipid-linked oligosaccharides (LLOs) including OSTs and LLOs associated with synthesis of bacterial O antigens.

  所公开的是无细胞合成糖基化蛋白质的方法、系统、组件和组合物。糖基化蛋白质可用于疫苗，包括抗菌疫苗。糖基化蛋白质可包括与载体共轭的细菌多糖，可用于在免疫宿主中产生针对与载体共轭的多糖的免疫反应。糖基化蛋白质可在无细胞糖蛋白合成（CFGpS）系统中合成，该系统使用富含糖蛋白合成成分的原核细胞裂解物，如低聚糖转移酶（OST）和脂联低聚糖（LLO），包括与合成细菌 O 抗原有关的 OST 和 LLO。
• Compositions and methods for rapid in vitro synthesis of bioconjugate vaccines in vitro via production and N-glycosylation of protein carriers in detoxified prokaryotic cell lysates
  申请人：Northwestern University

  公开号：US11530432B2

  公开（公告）日：2022-12-20

  Disclosed are methods, systems, components, and compositions for cell-free synthesis of glycosylated carrier proteins. The glycosylated carrier proteins may be utilized in vaccines, including anti-bacterial vaccines. The glycosylated carrier proteins may include a bacterial polysaccharide conjugated to a carrier, which may be utilized to generate an immune response in an immunized host against the polysaccharide conjugated to the carrier. The glycosylated carrier proteins may be synthesized in cell-free glycoprotein synthesis (CFGpS) systems using prokaryote cell lysates that are enriched in components for glycoprotein synthesis such as oligosaccharyltransferases (OSTs) and lipid-linked oligosaccharides (LLOs) including OSTs and LLOs associated with synthesis of bacterial O antigens.

  所公开的是无细胞合成糖基化载体蛋白的方法、系统、组件和组合物。糖基化载体蛋白可用于疫苗，包括抗菌疫苗。糖基化载体蛋白可包括与载体共轭的细菌多糖，可用于在免疫宿主中产生针对与载体共轭的多糖的免疫反应。糖基化载体蛋白可在无细胞糖蛋白合成（CFGpS）系统中合成，该系统使用富含糖蛋白合成成分的原核细胞裂解物，如低聚糖转移酶（OST）和脂联低聚糖（LLO），包括与合成细菌 O 抗原有关的 OST 和 LLO。
• IMMUNOGENIC SEQUENCES
  申请人：The Secretary of State for Defence

  公开号：EP1509607A1

  公开（公告）日：2005-03-02
• BIOCONJUGATE VACCINES' SYNTHESIS IN PROKARYOTIC CELL LYSATES
  申请人：Northwestern University

  公开号：EP3908669A1

  公开（公告）日：2021-11-17