通过叠氮化物与保护的和天然的碳水化合物供体的还原糖基化反应直接合成β-N-糖苷。
Direct synthesis of β-N-glycosides by the reductive glycosylation of azides with protected and native carbohydrate donors.
机构信息
Department of Chemistry, Yale University, 225 Prospect Street, New Haven, CT 06520-8107, USA.
出版信息
Angew Chem Int Ed Engl. 2013 Jun 3;52(23):6068-71. doi: 10.1002/anie.201301264. Epub 2013 Apr 22.
Abstract
A simple and straightforward method for the stereocontrolled synthesis of β-linked N-glycosides uses alkyl and aryl azides as the nitrogen source. The N-glycosides are formed in high yields and with high β selectivities (typically >70% yield, >15:1 β:α selectivity). This approach is also amenable to the synthesis of N-glycosylated amino acids and peptides (see example, Fmoc=9-fluorenylmethoxycarbonyl).
摘要
一种简单直接的β-构型控制的 N-糖基化方法，使用烷基和芳基叠氮化物作为氮源。该方法以高产率和高β选择性（典型产率>70%，β：α 选择性>15：1）得到 N-糖苷。这种方法也适用于 N-糖基化氨基酸和肽的合成（见实例，Fmoc=9-芴甲氧羰基）。
相似文献
1
Direct synthesis of β-N-glycosides by the reductive glycosylation of azides with protected and native carbohydrate donors.通过叠氮化物与保护的和天然的碳水化合物供体的还原糖基化反应直接合成β-N-糖苷。
Angew Chem Int Ed Engl. 2013 Jun 3;52(23):6068-71. doi: 10.1002/anie.201301264. Epub 2013 Apr 22.
2
One-pot azidochlorination of glycals.一锅法糖醛的叠氮氯代反应。
Org Lett. 2011 Feb 18;13(4):545-7. doi: 10.1021/ol102750h. Epub 2011 Jan 18.
3
Scope and limitations of 2-deoxy- and 2,6-dideoxyglycosyl bromides as donors for the synthesis of β-2-deoxy- and β-2,6-dideoxyglycosides.2-脱氧和 2,6-二脱氧糖基溴化物作为合成β-2-脱氧和β-2,6-二脱氧糖苷的供体的范围和局限性。
Org Lett. 2014 May 16;16(10):2776-9. doi: 10.1021/ol501101f. Epub 2014 May 1.
4
Divergent synthesis of three classes of aryl N-glycosides by solvent control.通过溶剂控制实现三类芳基 N-糖苷的发散合成。
J Org Chem. 2009 Jan 16;74(2):685-95. doi: 10.1021/jo8020133.
5
Synthesis and Stereocontrolled Equatorially Selective Glycosylation Reactions of a Pseudaminic Acid Donor: Importance of the Side-Chain Conformation and Regioselective Reduction of Azide Protecting Groups.假氨基糖供体的合成及立体选择性赤道糖苷化反应：侧链构象的重要性和叠氮保护基的区域选择性还原。
J Am Chem Soc. 2018 Nov 7;140(44):15008-15015. doi: 10.1021/jacs.8b09654. Epub 2018 Oct 25.
6
Stereoselective synthesis of 2-deoxy-β-C-aryl/alkyl glycosides using Prins cyclization: Application in the synthesis of C-disaccharides and differently protected C-aryl glycosides.使用普林斯环化反应立体选择性合成2-脱氧-β-C-芳基/烷基糖苷：在C-二糖和不同保护的C-芳基糖苷合成中的应用。
Carbohydr Res. 2018 Oct;468:64-68. doi: 10.1016/j.carres.2018.08.013. Epub 2018 Aug 22.
7
Synthesis of 2-Deoxyglycosides Bearing Free Hydroxyl Substituents on the Glycosyl Donor.2-脱氧糖基供体上带有游离羟基取代基的糖苷的合成。
J Org Chem. 2022 Aug 19;87(16):10768-10790. doi: 10.1021/acs.joc.2c01003. Epub 2022 Aug 3.
8
Ferrier-type N-glycosylation: synthesis of N-glycosides of enone sugars.费里埃型 N-糖基化：烯酮糖 N-糖苷的合成。
J Org Chem. 2013 Feb 1;78(3):1293-9. doi: 10.1021/jo302619b. Epub 2013 Jan 15.
9
Protecting group free glycosidations using p-toluenesulfonohydrazide donors.使用对甲苯磺酰肼供体进行无保护基糖苷化反应
Org Lett. 2008 Aug 21;10(16):3461-3. doi: 10.1021/ol801232f. Epub 2008 Jul 11.
10
A novel synthesis of beta-D-mannopyranosyl azide by phase transfer catalysis.通过相转移催化法合成β-D-甘露吡喃糖叠氮化物的新方法。
Carbohydr Res. 2009 Jan 26;344(2):240-4. doi: 10.1016/j.carres.2008.10.027. Epub 2008 Nov 5.
引用本文的文献
1
Allyl Cyanate/Isocyanate Rearrangement in Glycals: Stereoselective Synthesis of 1-Amino and Diamino Sugar Derivatives.糖醛内的烯丙基氰酸酯/异氰酸酯重排：1-氨基和二氨基糖衍生物的立体选择性合成。
Org Lett. 2020 Nov 20;22(22):9041-9046. doi: 10.1021/acs.orglett.0c03438. Epub 2020 Nov 4.
本文引用的文献
1
Probing the frontiers of glycoprotein synthesis: the fully elaborated β-subunit of the human follicle-stimulating hormone.探索糖蛋白合成的前沿：人促卵泡激素完全成熟的β亚基
Angew Chem Int Ed Engl. 2012 Jan 23;51(4):975-9. doi: 10.1002/anie.201107482. Epub 2011 Dec 9.
2
Warfarin glycosylation invokes a switch from anticoagulant to anticancer activity.华法林糖基化引发了从抗凝活性到抗癌活性的转变。
ChemMedChem. 2011 Aug 1;6(8):1347-50. doi: 10.1002/cmdc.201100178. Epub 2011 Jun 28.
3
The expanding horizons of asparagine-linked glycosylation.天冬酰胺连接糖基化的扩展视野。
Biochemistry. 2011 May 31;50(21):4411-26. doi: 10.1021/bi200346n. Epub 2011 May 4.
4
Encouraging progress in the ω-aspartylation of complex oligosaccharides as a general route to β-N-linked glycopolypeptides.鼓励复杂寡糖的 ω-天冬氨酰化作为制备 β-N-连接糖肽的一般途径取得进展。
J Am Chem Soc. 2011 Feb 9;133(5):1597-602. doi: 10.1021/ja110115a. Epub 2011 Jan 5.
5
Recent Departures in the Synthesis of Peptides and Glycopeptides.肽和糖肽合成的最新进展。
Tetrahedron. 2009 Nov 7;65(45):9047-9065. doi: 10.1016/j.tet.2009.09.032.
6
Total synthesis of the 2,6-sialylated immunoglobulin G glycopeptide fragment in homogeneous form.以均相形式对 2,6-唾液酸化免疫球蛋白 G 糖肽片段的全合成。
J Am Chem Soc. 2009 Nov 25;131(46):16669-71. doi: 10.1021/ja907136d.
7
Synthesis of the fully glycosylated cyclohexenone core of lomaiviticin A.洛马维汀A完全糖基化环己烯酮核心的合成。
Org Lett. 2009 Oct 1;11(19):4322-5. doi: 10.1021/ol901710b.
8
Glycoprotein synthesis: an update.糖蛋白合成：最新进展。
Chem Rev. 2009 Jan;109(1):131-63. doi: 10.1021/cr078291i.
9
The ansacarbamitocins: polar ansamitocin derivatives.安杀霉素类：极性安莎霉素衍生物。
J Nat Prod. 2007 Oct;70(10):1578-81. doi: 10.1021/np070275t. Epub 2007 Sep 25.
10
Colchicine glycorandomization influences cytotoxicity and mechanism of action.秋水仙碱糖基随机化影响细胞毒性和作用机制。
J Am Chem Soc. 2006 Nov 8;128(44):14224-5. doi: 10.1021/ja064686s.
Zotero 插件