5-glycolylamido-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosylonic acid | 80124-69-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-glycolylamido-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosylonic acid
• 英文别名: N-glycoloylneuraminic acid；N-glycolyl neuraminic acid；N-glycolylneuraminic acid；Neu5Gc；N-Glykoloyl-D-neuraminsaeure；N-Glykolyl-neuraminsaeure；N-Glycolyl-Neuraminic acid；(4S,5R,6R)-2,4-dihydroxy-5-[(2-hydroxyacetyl)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 80124-69-2
• 化学式: C₁₁H₁₉NO₁₀
• 分子量: 325.273
• InChiKey: FDJKUWYYUZCUJX-PGIATKPXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  197
• 氢给体数：
  8
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5-glycolylamido-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosylonic acid 在 chST₆GalNAc-I 、 ST₃-CMPNeu₅Ac-synthetase fusion protein 、 三羟甲基氨基甲烷盐酸盐 、 magnesium chloride 作用下， 以 水 为溶剂， 反应 25.0h， 生成
  参考文献：
  名称：

  Efficient Chemoenzymatic Synthesis of O-Linked Sialyl Oligosaccharides

  摘要：

  The tumor associated Tn (GalNAcalpha(1-1)-Thr/Ser)- and T (Galbeta(1-3)-GalNAcalpha(1-1)Thr/Ser)antigens and their sialylated derivatives are present on the surface of many cancer cells. Preparative synthesis of these sialylated T- and Tn-structures has been achieved mainly from a chemical synthetic approach due to the lack of the required glycosyltransferases. We demonstrate a flexible and efficient chemoenzymatic approach for using recombinant sialyltransferases including a chicken GalNAcalpha2,6-sialyltransferase (chST6GalNAc1) and a porcine Galbeta(1-3)GalNAcalpha-2,3-sialyltransferase (pST3Gal 1). Using these enzymes, the common O-linked sialosides Neu5Acalpha(2-6)GalNAcalpha(1-1)Thr, Galbeta(1-3)[Neu5Acalpha(26)]GalNAcalpha(1-1)Thr, Neu5Acalpha(2-3)Galbeta(1-3)GalNAcalpha(1-1)Thr, and Neu5Acalpha(2-3)Galbeta(1-3)[Neu5Acalpha(-26)]GalNAcalpha(1-1)Thr were readily prepared at preparative scale. The chST6GalNAc I was found to require at least one amino acid (Thr/Ser) for optimal activity, and is thus an ideal catalyst for synthesis of synthetic glycopeptides and glycoconjugates with O-linked glycans.

  DOI：

  10.1021/ja017881+
• 作为产物：
  描述：

  sodium pyruvate 、 N-glycolylmannosamine 在 pyruvate lyase 作用下， 反应 20.0h， 以50%的产率得到5-glycolylamido-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosylonic acid
  参考文献：
  名称：

  Chemo-enzymatic synthesis of the carbohydrate antigen N-glycolylneuraminic acid from glucose

  摘要：

  N-Glycolylneuraminic acid (Neu5Gc) is a non-human sialic acid, which may play a significant role in human pathologies, such as cancer and vascular disease. Further studies into the role of Neu5Gc in human disease are hindered by limited sources of this carbohydrate. Using a chemo-enzymatic approach, Neu5Gc was accessed in six steps from glucose. The synthesis allows access to gram-scale quantities quickly and economically and produces Neu5Gc in superior quality to commercial sources. Finally, we demonstrate that the synthesized Neu5Gc can be incorporated into the cell glycocalyx of human cells, which do not naturally synthesize this sugar. The synthesis produces Neu5Gc suitable for in vitro or in vivo use. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.04.003

文献信息

• Chemoenzymatic synthesis and biological evaluation of ganglioside GM3 and lyso-GM3 as potential agents for cancer therapy
  作者：Tingshen Li、Xiaodan Wang、Peijie Dong、Peng Yu、Yongmin Zhang、Xin Meng

  DOI：10.1016/j.carres.2021.108431

  日期：2021.11

  A highly efficient chemoenzymatic method for synthesizing ganglioside GM3 and lyso-GM3 was reported here. Enzymatic extension of the chemically synthesized lactosyl sphingosine using efficient one-pot multienzyme (OPME) reaction allowed glycosylation to be carried out in aqueous solutions realizing the greening of reactions. Ganglioside GM3 was synthesized through 10 steps with a total yield of 22%

  本文报道了一种高效的化学酶法合成神经节苷脂 GM3 和 lyso-GM3。使用高效的一锅多酶（OPME）反应对化学合成的乳糖基鞘氨醇进行酶促延伸，使得糖基化可以在水溶液中进行，实现了反应的绿色化。神经节苷脂GM3经过10步合成，总收率为22%。 Lyso-GM3 对于各种衍生化非常有用。抗增殖活性研究表明，这些带有鞘氨醇的化合物14 – 16比相应的带有神经酰胺的 lyso-GM3 表现出更强的效力。所有神经节苷脂GM3和lyso-GM3均能有效抑制黑色素瘤B16-F10细胞的迁移。这些化学酶法合成的GM3和lyso-GM3表现出抗肿瘤活性，为寻找新的抗肿瘤药物用于癌症治疗提供了有价值的前景。
• Chemoenzymatic Assembly of Mammalian O-Mannose Glycans
  作者：Caicai Meng、Aniruddha Sasmal、Yan Zhang、Tian Gao、Chang-Cheng Liu、Naazneen Khan、Ajit Varki、Fengshan Wang、Hongzhi Cao

  DOI：10.1002/anie.201804373

  日期：2018.7.16

  O‐Mannose glycans account up to 30 % of total O‐glycans in the brain. Previous synthesis and functional studies have only focused on the core M3 O‐mannose glycans of α‐dystroglycan, which are a causative factor for various muscular diseases. In this study, a highly efficient chemoenzymatic strategy was developed that enabled the first collective synthesis of 63 core M1 and core M2 O‐mannose glycans

  O-甘露糖聚糖占大脑中O-聚糖总量的30％。先前的合成和功能研究仅集中于α-营养不良的核心M3 O-甘露糖聚糖，这是各种肌肉疾病的致病因素。在这项研究中，开发了一种高效的化学酶促策略，该策略能够首次集体合成63个核心M1和核心M2 O-甘露糖聚糖。这种化学酶学策略的特点是，对五个精心设计的核心结构进行了克级化学合成，并通过三个酶模块对核心结构进行了多样性导向的修饰，从而以线性顺序提供了58个复杂的O-甘露糖聚糖，且不超过四个步骤。合成的O-甘露糖聚糖与一组凝集素，抗体，
• Synthesis of 9-O-acyl- and 4-O-acetyl-sialic acids
  作者：Haruo Ogura、Kimio Furuhata、Shingo Sato、Katsuko Anazawa、Masayoshi Itoh、Yoshiyasu Shitori

  DOI：10.1016/0008-6215(87)80269-0

  日期：1987.9

  N-glycoloyl-neuraminic acid, and O-(5-acetamido-3,5-dideoxy-D-glycero-alpha- and beta-D-galacto-2-nonulopyranosylonic acid)-(2----6)-O-beta-D-galactopyranosyl-(1----4)-D-glucopyranose were regioselectively synthesized by use of ortho esters. In addition, 5-acetamido-4-O-acetyl-D-glycero-D-galacto-2-nonulopyranosonic acid was prepared starting from the benzyl and methyl esters of N-acetylneuraminic acid.

  N-乙酰基和N-糖基神经氨酸的各种9-O-酰基衍生物，以及O-（5-乙酰氨基-3,5-二脱氧-D-甘油-α-和β-D-半乳糖-2-壬基吡喃戊二酸通过使用原酸酯区域选择性地合成酸）-（2 ---- 6）-O-β-D-吡喃半乳糖基-（1 ---- 4）-D-吡喃葡萄糖。另外，从N-乙酰神经氨酸的苄基和甲基酯开始制备5-乙酰氨基-4-O-乙酰基-D-甘油-D-半乳糖基-2-壬基吡喃磺酸。
• Systematic chemoenzymatic synthesis of O-sulfated sialyl Lewis x antigens
  作者：Abhishek Santra、Hai Yu、Nova Tasnima、Musleh M. Muthana、Yanhong Li、Jie Zeng、Nicholas J. Kenyon、Angelique Y. Louie、Xi Chen

  DOI：10.1039/c5sc04104j

  日期：——

  O-Sulfated sialyl Lewisxantigens containing different sialic acid forms were chemoenzymatically synthesized using a bacterial sialyltransferase mutant.

  使用细菌唾液酸转移酶突变体，通过化学酶法合成含有不同唾液酸形式的O-硫酸基的硫酸基的西阿尔路易斯X抗原。
• Synthesis of a Sialyl Lewis X Ganglioside Analogue Containing<i>N</i>-Glycolyl in Place of the<i>N</i>-Acetyl Group in the<i>N</i>-Acetylneuraminic Acid Residue
  作者：Akira Hasegawa、Akira Uchimura、Hideharu Ishida、Makoto Kiso

  DOI：10.1271/bbb.59.1091

  日期：1995.1

  A sialyl Lewis X ganglioside analogue containing 5-glycolylamido-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosylonic acid in place of N-acetylneurarninic acid was synthesized, clarifying the structural requirement for an N-acetyl group in the sialic acid moiety for selectin recognition.

  合成了一种含有 5-甘氨酰氨基-3,5-二脱氧-D-甘油-D-半乳糖-2-nonulopyranosylonic 酸而不是 N-acetylneurarninic 酸的 sialyl Lewis X 神经节苷脂类似物，明确了选择素识别中对 sialic 酸分子中 N-acetyl 基团的结构要求。