• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利：CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法，用中文像聊天一样搜索，搜遍4000万医学文献。AI智能推荐，让科研检索更轻松。

立即免费搜索

文件翻译

保留排版，准确专业，支持PDF/Word/PPT等文件格式，支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述，25分钟生成高质量综述，智能提取关键信息，辅助科研写作。

立即免费体验

I 型和 II 型 LacNAc 重复寡糖作为肿瘤相关 Lewis 抗原骨架的合成。

Synthesis of Type-I and Type-II LacNAc-Repeating Oligosaccharides as the Backbones of Tumor-Associated Lewis Antigens.

机构信息

Department of Chemistry, National Taiwan University, Taipei, Taiwan.

Institute of Biological Chemistry, Academia Sinica, Taipei, Taiwan.

出版信息

Front Immunol. 2022 Feb 23;13:858894. doi: 10.3389/fimmu.2022.858894. eCollection 2022.

DOI:10.3389/fimmu.2022.858894
PMID:35281035
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8905443/
Abstract

Type-I and Type-II LacNAc are Gal-GlcNAc disaccharides bearing a β1,3- or β1,4-linkage respectively. They exist as the backbones of Lewis antigens that are highly expressed in several cancers. Owing to the promise of developing carbohydrate-based anti-cancer vaccines, glycan synthesis at a large scale is indeed an important task. Synthesis of Type-I and Type-II tandem repeat oligomers has been hampered by the presence of GlcNAc residues. Particularly, -protecting group plays a determining role in affecting glycosyl donor's reactivity and acceptor's nucleophilicity. This review discusses several representative studies that assembled desirable glycans in an efficient manner, such as chemoselective one-pot synthesis and chemoenzymatic methods. Additionally, we also highlight solutions that have been offered to tackle long-lasting problems, e.g., prevention of the oxazoline formation and change of donor/acceptor reactivity. In retrospect of scientific achievements, we present the current restrictions and remaining challenges in this less explored frontier.

摘要

I 型和 II 型 LacNAc 分别是带有β1,3-或β1,4-键的 Gal-GlcNAc 二糖。它们作为Lewis 抗原的骨架存在，Lewis 抗原在几种癌症中高度表达。由于开发基于碳水化合物的抗癌疫苗具有广阔前景，因此大规模进行糖合成确实是一项重要任务。I 型和 II 型串联重复寡聚物的合成受到 GlcNAc 残基的阻碍。特别是，-保护基在影响糖基供体的反应性和受体的亲核性方面起着决定性作用。本文综述了几种有代表性的研究，这些研究以有效的方式组装了所需的聚糖，如化学选择性一锅合成和化学酶法。此外，我们还强调了为解决长期存在的问题而提供的解决方案，例如防止恶唑啉的形成和改变供体/受体的反应性。在回顾科学成就的基础上，我们提出了在这个探索较少的前沿领域目前存在的限制和挑战。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5466/8905443/dcb933e4de18/fimmu-13-858894-s011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5466/8905443/4f416066aef7/fimmu-13-858894-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5466/8905443/6958f5959bb4/fimmu-13-858894-s001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5466/8905443/817a064ce949/fimmu-13-858894-s002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5466/8905443/ccc14a5b740d/fimmu-13-858894-s003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5466/8905443/fe469bbd9928/fimmu-13-858894-s004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5466/8905443/70612ae2107e/fimmu-13-858894-s005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5466/8905443/f7fde0c542ab/fimmu-13-858894-s006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5466/8905443/79b6091d41f5/fimmu-13-858894-s007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5466/8905443/661ac978b730/fimmu-13-858894-s008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5466/8905443/15f9ecd0d8aa/fimmu-13-858894-s009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5466/8905443/2843756e766c/fimmu-13-858894-s010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5466/8905443/beb1e7aa36c9/fimmu-13-858894-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5466/8905443/dcb933e4de18/fimmu-13-858894-s011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5466/8905443/4f416066aef7/fimmu-13-858894-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5466/8905443/6958f5959bb4/fimmu-13-858894-s001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5466/8905443/817a064ce949/fimmu-13-858894-s002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5466/8905443/ccc14a5b740d/fimmu-13-858894-s003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5466/8905443/fe469bbd9928/fimmu-13-858894-s004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5466/8905443/70612ae2107e/fimmu-13-858894-s005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5466/8905443/f7fde0c542ab/fimmu-13-858894-s006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5466/8905443/79b6091d41f5/fimmu-13-858894-s007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5466/8905443/661ac978b730/fimmu-13-858894-s008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5466/8905443/15f9ecd0d8aa/fimmu-13-858894-s009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5466/8905443/2843756e766c/fimmu-13-858894-s010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5466/8905443/beb1e7aa36c9/fimmu-13-858894-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/5466/8905443/dcb933e4de18/fimmu-13-858894-s011.jpg

相似文献

1
Synthesis of Type-I and Type-II LacNAc-Repeating Oligosaccharides as the Backbones of Tumor-Associated Lewis Antigens.I 型和 II 型 LacNAc 重复寡糖作为肿瘤相关 Lewis 抗原骨架的合成。
Front Immunol. 2022 Feb 23;13:858894. doi: 10.3389/fimmu.2022.858894. eCollection 2022.
2
Synthesis of a new nanomolar saccharide inhibitor of lymphocyte adhesion: different polylactosamine backbones present multiple sialyl Lewis x determinants to L-selectin in high-affinity mode.一种新型纳摩尔级淋巴细胞黏附糖抑制剂的合成：不同的聚乳糖胺主链以高亲和力模式向L-选择素呈现多个唾液酸化路易斯x决定簇。
Glycobiology. 1997 Jun;7(4):453-61. doi: 10.1093/glycob/7.4.453-c.
3
Donor Preactivation-Based Glycan Assembly: from Manual to Automated Synthesis.基于供体预活化的聚糖组装：从手动合成到自动合成
Acc Chem Res. 2024 Jun 4;57(11):1577-1594. doi: 10.1021/acs.accounts.4c00072. Epub 2024 Apr 15.
4
In vitro biosynthesis of a decasaccharide prototype of multiply branched polylactosaminoglycan backbones.多分支聚乳糖胺聚糖主链十糖原型的体外生物合成。
Biochemistry. 1997 Jun 10;36(23):7026-36. doi: 10.1021/bi9627673.
5
Carbohydrate specificity of a galectin from chicken liver (CG-16).鸡肝半乳糖凝集素（CG-16）的碳水化合物特异性
Biochem J. 2001 Sep 15;358(Pt 3):529-38. doi: 10.1042/0264-6021:3580529.
6
Enzymatic Synthesis of N-Acetyllactosamine (LacNAc) Type 1 Oligomers and Characterization as Multivalent Galectin Ligands.酶法合成 N-乙酰乳糖胺（LacNAc）1 型低聚糖及其作为多价半乳糖凝集素配体的特性。
Molecules. 2017 Aug 10;22(8):1320. doi: 10.3390/molecules22081320.
7
Helicobacter pylori β1,3-N-acetylglucosaminyltransferase for versatile synthesis of type 1 and type 2 poly-LacNAcs on N-linked, O-linked and I-antigen glycans.幽门螺杆菌β1,3-N-乙酰氨基葡萄糖基转移酶用于在 N 连接、O 连接和 I 抗原聚糖上的灵活合成 1 型和 2 型多-LacNAc。
Glycobiology. 2012 Nov;22(11):1453-64. doi: 10.1093/glycob/cws101. Epub 2012 Jul 11.
8
Syntheses of Lewis(x) and dimeric Lewis(x): construction of branched oligosaccharides by a combination of preactivation and reactivity based chemoselective one-pot glycosylations.Lewis(x) 及二聚体Lewis(x) 的合成：通过预活化与基于反应性的化学选择性一锅法糖基化反应相结合构建支链寡糖。
J Org Chem. 2007 Nov 9;72(23):8958-61. doi: 10.1021/jo701694k. Epub 2007 Oct 16.
9
Biosynthesis of the carbohydrate antigenic determinants, Globo H, blood group H, and Lewis b: a role for prostate cancer cell alpha1,2-L-fucosyltransferase.碳水化合物抗原决定簇Globo H、血型H和Lewis b的生物合成：前列腺癌细胞α1,2-L-岩藻糖基转移酶的作用
Glycobiology. 2002 Mar;12(3):153-62. doi: 10.1093/glycob/12.3.153.
10
Threshold of Thioglycoside Reactivity Difference Is Critical for Efficient Synthesis of Type I Oligosaccharides by Chemoselective Glycosylation.硫代糖苷反应性差异的阈值对于通过化学选择性糖基化高效合成 I 型寡糖至关重要。
J Org Chem. 2021 Jan 1;86(1):892-916. doi: 10.1021/acs.joc.0c02422. Epub 2020 Dec 15.

引用本文的文献

1
Chemoenzymatic Synthesis of Tri-antennary N-Glycans Terminating in Sialyl-Lewis Reveals the Importance of Glycan Complexity for Influenza A Virus Receptor Binding.通过酶化学合成三触角 N-聚糖，终止于唾液酸化-Lewis，揭示了糖复合物对于流感 A 病毒受体结合的重要性。
Chemistry. 2024 Jun 6;30(32):e202401108. doi: 10.1002/chem.202401108. Epub 2024 May 8.
2
Metabolism-driven glycosylation represents therapeutic opportunities in interstitial lung diseases.代谢驱动的糖基化代表了间质性肺疾病的治疗机会。
Front Immunol. 2024 Mar 14;15:1328781. doi: 10.3389/fimmu.2024.1328781. eCollection 2024.
3
Recombinant Human CD19 in CHO-K1 Cells: Glycosylation Patterns as a Quality Attribute of High Yield Processes.

本文引用的文献

1
Synthesis as an Expanding Resource in Human Milk Science.人乳科学中合成物作为一种扩展资源。
J Am Chem Soc. 2021 Aug 4;143(30):11277-11290. doi: 10.1021/jacs.1c05599. Epub 2021 Jul 23.
2
Aberrant protein glycosylation in cancer: implications in targeted therapy.癌症中的异常蛋白质糖基化：在靶向治疗中的意义。
Biochem Soc Trans. 2021 Apr 30;49(2):843-854. doi: 10.1042/BST20200763.
3
Automated Quantification of Hydroxyl Reactivities: Prediction of Glycosylation Reactions.羟基反应活性的自动化定量：糖基化反应的预测。
CHO-K1 细胞中的重组人 CD19：糖基化模式作为高产工艺的质量属性。
Int J Mol Sci. 2023 Jun 30;24(13):10891. doi: 10.3390/ijms241310891.
4
Innovative Metrics for Reporting and Comparing the Glycan Structural Profile in Biotherapeutics.创新的生物治疗药物聚糖结构谱报告和比较指标。
Molecules. 2023 Apr 7;28(8):3304. doi: 10.3390/molecules28083304.
5
ST3GalIV drives SLeX biosynthesis in gastrointestinal cancer cells and associates with cancer cell motility.ST3GalIV 在胃肠道癌细胞中驱动 SLeX 的生物合成，并与癌细胞的迁移能力相关。
Glycoconj J. 2023 Aug;40(4):421-433. doi: 10.1007/s10719-023-10113-y. Epub 2023 Apr 19.
Angew Chem Int Ed Engl. 2021 May 25;60(22):12413-12423. doi: 10.1002/anie.202013909. Epub 2021 Apr 21.
4
Threshold of Thioglycoside Reactivity Difference Is Critical for Efficient Synthesis of Type I Oligosaccharides by Chemoselective Glycosylation.硫代糖苷反应性差异的阈值对于通过化学选择性糖基化高效合成 I 型寡糖至关重要。
J Org Chem. 2021 Jan 1;86(1):892-916. doi: 10.1021/acs.joc.0c02422. Epub 2020 Dec 15.
5
Tumor-associated carbohydrates and immunomodulatory lectins as targets for cancer immunotherapy.肿瘤相关碳水化合物和免疫调节凝集素作为癌症免疫治疗的靶点。
J Immunother Cancer. 2020 Oct;8(2). doi: 10.1136/jitc-2020-001222.
6
Synthetic carbohydrate-based vaccines: challenges and opportunities.合成碳水化合物疫苗：挑战与机遇。
J Biomed Sci. 2020 Jan 3;27(1):9. doi: 10.1186/s12929-019-0591-0.
7
Automated glycan assembly of Lewis type I and II oligosaccharide antigens.路易斯I型和II型寡糖抗原的自动化聚糖组装
Chem Sci. 2019 Apr 29;10(21):5634-5640. doi: 10.1039/c9sc00768g. eCollection 2019 Jun 7.
8
Glycosylation in the Era of Cancer-Targeted Therapy: Where Are We Heading?癌症靶向治疗时代的糖基化：我们将走向何方？
Cancer Cell. 2019 Jul 8;36(1):6-16. doi: 10.1016/j.ccell.2019.06.006.
9
Acceptor reactivity in glycosylation reactions.糖基化反应中的受体反应活性。
Chem Soc Rev. 2019 Aug 27;48(17):4688-4706. doi: 10.1039/c8cs00369f.
10
Protecting-Group-Controlled Enzymatic Glycosylation of Oligo-N-Acetyllactosamine Derivatives.寡糖 N-乙酰乳糖胺衍生物的保护基控制酶糖基化反应。
Angew Chem Int Ed Engl. 2019 Jul 29;58(31):10547-10552. doi: 10.1002/anie.201903140. Epub 2019 Jul 1.