• 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

天然构型α-半乳糖苷棉子糖全合成免疫刺激剂α-半乳糖神经酰胺。

The total synthesis of immunostimulant α-galactosylceramides from naturally configured α-galactoside raffinose.

机构信息

College of Pharmacy, Nankai University, Tianjin 300071, China.

出版信息

Org Lett. 2011 Sep 2;13(17):4530-3. doi: 10.1021/ol201695n. Epub 2011 Aug 4.

DOI:10.1021/ol201695n
PMID:21815670
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3398385/
Abstract

The total synthesis of absolute anomeric confirmation α-galactosylceramide analogues from raffinose is described. Using the naturally occurring α-galactoside raffinose as the starting material, the easily maneuverable protocol without glycosylation reactions ensured the critical α-linkage in the product and simplified the synthetic procedures. The immunostimulatory activities of the new α-galactosylceramides were validated by both in vitro and in vivo NKT cell stimulation assays.

摘要

本文描述了从棉子糖中全合成绝对构型α-半乳糖基神经酰胺类似物的方法。以天然存在的α-半乳糖苷棉子糖为起始原料，采用无需糖苷化反应的易于操作的方案，确保了产物中关键的α-键合，并简化了合成步骤。通过体外和体内 NKT 细胞刺激实验验证了新型α-半乳糖神经酰胺的免疫刺激活性。

相似文献

1
The total synthesis of immunostimulant α-galactosylceramides from naturally configured α-galactoside raffinose.天然构型α-半乳糖苷棉子糖全合成免疫刺激剂α-半乳糖神经酰胺。
Org Lett. 2011 Sep 2;13(17):4530-3. doi: 10.1021/ol201695n. Epub 2011 Aug 4.
2
Synthesis of a glucosylated α-S-galactosylceramide as potential immunostimulant.
Carbohydr Res. 2017 Aug 7;448:43-47. doi: 10.1016/j.carres.2017.05.022. Epub 2017 Jun 1.
3
Synthesis of α-C-Galactosylceramide via Diastereoselective Aziridination: The New Immunostimulant 4'-epi-C-Glycoside of KRN7000.
Org Lett. 2016 Feb 19;18(4):808-11. doi: 10.1021/acs.orglett.6b00090. Epub 2016 Feb 4.
4
Synthesis of alpha-galactosyl ceramide, a potent immunostimulatory agent.强效免疫刺激剂α-半乳糖神经酰胺的合成。
J Org Chem. 2002 Jun 28;67(13):4559-64. doi: 10.1021/jo0201530.
5
The first synthesis of a thioglycoside analogue of the immunostimulant KRN7000.免疫刺激剂KRN7000的硫代糖苷类似物的首次合成。
Org Lett. 2008 Oct 16;10(20):4641-4. doi: 10.1021/ol8019555. Epub 2008 Sep 23.
6
Expedient synthesis of the alpha-C-glycoside analogue of the immunostimulant galactosylceramide (KRN7000).
Org Lett. 2006 Jul 20;8(15):3375-8. doi: 10.1021/ol0613057.
7
Total synthesis of α-1C-galactosylceramide, an immunostimulatory C-glycosphingolipid, and confirmation of the stereochemistry in the first-generation synthesis.α-1C-半乳糖基神经酰胺的全合成，一种免疫刺激的 C-糖鞘脂，以及第一代合成中立体化学的确认。
J Org Chem. 2011 Nov 4;76(21):8588-98. doi: 10.1021/jo201450s. Epub 2011 Oct 4.
8
Intramolecular nitrogen delivery for the synthesis of C-glycosphingolipids. Application to the C-glycoside of the immunostimulant KRN7000.分子内氮供体在 C-糖脂合成中的应用。在免疫刺激剂 KRN7000 的 C-糖苷中的应用。
Org Lett. 2014 Mar 7;16(5):1466-9. doi: 10.1021/ol5002686. Epub 2014 Feb 21.
9
Alpha-c-galactosylceramides: synthesis and immunology.
Acc Chem Res. 2006 Oct;39(10):692-701. doi: 10.1021/ar050006z.
10
Synthesis of all stereoisomers of KRN7000, the CD1d-binding NKT cell ligand.CD1d结合性NKT细胞配体KRN7000所有立体异构体的合成。
Bioorg Med Chem Lett. 2008 Jul 15;18(14):3906-9. doi: 10.1016/j.bmcl.2008.06.036. Epub 2008 Jun 14.

引用本文的文献

1
A Review Discussing Synthesis and Translational Studies of Medicinal Agents Targeting Sphingolipid Pathways.一篇关于靶向鞘脂途径的药物合成与转化研究的综述
Biomolecules. 2025 Jul 16;15(7):1022. doi: 10.3390/biom15071022.
2
Thermodynamic and Structural Behavior of α-Galactosylceramide and C6-Functionalized α-GalCer in 2D Layers at the Air-Liquid Interface.α-半乳糖神经酰胺和 C6 功能化 α-半乳糖神经鞘氨醇在空气-液相界面二维层中的热力学和结构行为。
Chembiochem. 2020 Jan 15;21(1-2):241-247. doi: 10.1002/cbic.201900491. Epub 2019 Nov 7.

本文引用的文献

1
Introduction of aromatic group on 4'-OH of α-GalCer manipulated NKT cell cytokine production.介绍在 α-GalCer 的 4'-OH 上引入芳基基团对 NKT 细胞细胞因子产生的影响。
Bioorg Med Chem. 2011 Apr 15;19(8):2767-76. doi: 10.1016/j.bmc.2010.11.061. Epub 2010 Dec 2.
2
Adaptability of the semi-invariant natural killer T-cell receptor towards structurally diverse CD1d-restricted ligands.半不变自然杀伤T细胞受体对结构多样的CD1d限制性配体的适应性。
EMBO J. 2009 Nov 18;28(22):3579-90. doi: 10.1038/emboj.2009.286. Epub 2009 Oct 8.
3
Differential recognition of CD1d-alpha-galactosyl ceramide by the V beta 8.2 and V beta 7 semi-invariant NKT T cell receptors.Vβ8.2和Vβ7半不变自然杀伤T细胞受体对CD1d-α-半乳糖神经酰胺的差异识别
Immunity. 2009 Jul 17;31(1):47-59. doi: 10.1016/j.immuni.2009.04.018.
4
Synthesis and in vivo evaluation of 4-deoxy-4,4-difluoro-KRN7000.
Org Lett. 2008 Oct 16;10(20):4433-6. doi: 10.1021/ol801663m. Epub 2008 Sep 18.
5
Synthesis of all stereoisomers of KRN7000, the CD1d-binding NKT cell ligand.CD1d结合性NKT细胞配体KRN7000所有立体异构体的合成。
Bioorg Med Chem Lett. 2008 Jul 15;18(14):3906-9. doi: 10.1016/j.bmcl.2008.06.036. Epub 2008 Jun 14.
6
Alpha-lactosylceramide as a novel "sugar-capped" CD1d ligand for natural killer T cells: biased cytokine profile and therapeutic activities.α-乳糖神经酰胺作为一种新型的天然杀伤性T细胞“糖封端”CD1d配体：偏向性细胞因子谱及治疗活性
Chembiochem. 2008 Jun 16;9(9):1423-30. doi: 10.1002/cbic.200700625.
7
Preparation of partially benzylated mono-, di-, and trisaccharides by selective cleavage of the beta-fructofuranosidic linkage in fully benzylated sucrose and sucrose-related oligosaccharides under acidic conditions.在酸性条件下，通过选择性裂解全苄基化蔗糖及蔗糖相关寡糖中的β-呋喃果糖苷键来制备部分苄基化的单糖、二糖和三糖。
Carbohydr Res. 2008 Jun 9;343(8):1366-72. doi: 10.1016/j.carres.2008.03.024. Epub 2008 Mar 25.
8
De novo synthesis of a D-galacturonic acid thioglycoside as key to the total synthesis of a glycosphingolipid from Sphingomonas yanoikuyae.
Org Lett. 2008 Apr 17;10(8):1573-6. doi: 10.1021/ol800227b. Epub 2008 Mar 26.
9
Highly efficient and stereoselective synthesis of beta-glycolipids.β-糖脂的高效立体选择性合成
Org Biomol Chem. 2008 Feb 7;6(3):443-6. doi: 10.1039/b718521a. Epub 2007 Dec 11.
10
Synthesis and structure-activity relationship study of isoglobotrihexosylceramide analogues.异球三己糖神经酰胺类似物的合成及构效关系研究
J Org Chem. 2007 Dec 21;72(26):9914-23. doi: 10.1021/jo701539k. Epub 2007 Nov 17.