人乳寡糖的化学合成：乳-N-新四糖（Galβ1 → 4GlcNAcβ1→）3,6Galβ1 → 4Glc。
Chemical synthesis of human milk oligosaccharides: lacto-N-neohexaose (Galβ1 → 4GlcNAcβ1→) 3,6Galβ1 → 4Glc.
机构信息
Department of Chemistry and Biochemistry, University of Missouri - St. Louis, One University Boulevard, St Louis, Missouri 63121, USA.
出版信息
Org Biomol Chem. 2020 Mar 4;18(9):1747-1753. doi: 10.1039/d0ob00172d.
Abstract
The first chemical synthesis of lacto-N-neohexaose (LNnH) has been completed using a convergent synthetic strategy. The reaction conditions and donor-acceptor combinations have been carefully refined to minimize side reactions and achieve high yields in all glycosylation steps. Lacto-N-neotetraose, another common human milk oligosaccharide, was also synthesized en route to the target LNnH.
摘要
首次采用汇聚式合成策略完成了乳-N-新四糖（LNnH）的化学全合成。仔细优化了反应条件和供体-受体组合，以最大限度地减少副反应，并在所有糖基化步骤中实现高产率。在合成目标 LNnH 的过程中，还合成了另一种常见的人乳寡糖——乳-N-四糖。
相似文献
1
Chemical synthesis of human milk oligosaccharides: lacto-N-neohexaose (Galβ1 → 4GlcNAcβ1→) 3,6Galβ1 → 4Glc.人乳寡糖的化学合成：乳-N-新四糖（Galβ1 → 4GlcNAcβ1→）3,6Galβ1 → 4Glc。
Org Biomol Chem. 2020 Mar 4;18(9):1747-1753. doi: 10.1039/d0ob00172d.
2
Chemical Synthesis of Human Milk Oligosaccharides: Lacto--hexaose Galβ1→3GlcNAcβ1→3 [Galβ1→4GlcNAcβ1→6] Galβ1→4Glc.人乳寡糖的化学合成：乳六糖 Galβ1→3GlcNAcβ1→3[Galβ1→4GlcNAcβ1→6]Galβ1→4Glc。
J Org Chem. 2019 Dec 20;84(24):16192-16198. doi: 10.1021/acs.joc.9b02701. Epub 2019 Dec 5.
3
The chemical synthesis of human milk oligosaccharides: Lacto-N-neotetraose (Galβ1→4GlcNAcβ1→3Galβ1→4Glc).人乳寡糖的化学合成：乳-N-新四糖（Galβ1→4GlcNAcβ1→3Galβ1→4Glc）。
Carbohydr Res. 2019 Sep 1;483:107743. doi: 10.1016/j.carres.2019.107743. Epub 2019 Jul 11.
4
The chemical synthesis of human milk oligosaccharides: Lacto-N-tetraose (Galβ1→3GlcNAcβ1→3Galβ1→4Glc).人乳寡糖的化学合成：乳-N-四糖（半乳糖β1→3-N-乙酰氨基葡萄糖β1→3-半乳糖β1→4-葡萄糖）。
Carbohydr Res. 2019 Dec 1;486:107824. doi: 10.1016/j.carres.2019.107824. Epub 2019 Sep 25.
5
Chemoenzymatic Synthesis of Asymmetrically Branched Human Milk Oligosaccharide Lacto--Hexaose.不对称支链人乳寡糖乳糖-N-己糖的化学酶法合成
Front Chem. 2022 May 31;10:905105. doi: 10.3389/fchem.2022.905105. eCollection 2022.
6
Biochemical characterization of Helicobacter pylori α1-3-fucosyltransferase and its application in the synthesis of fucosylated human milk oligosaccharides.幽门螺旋杆菌α1-3-岩藻糖基转移酶的生化特性及其在人乳寡糖岩藻糖基化合成中的应用。
Carbohydr Res. 2019 Jul 1;480:1-6. doi: 10.1016/j.carres.2019.05.007. Epub 2019 May 16.
7
Design of an α-L-transfucosidase for the synthesis of fucosylated HMOs.用于合成岩藻糖基化人乳寡糖的α-L-岩藻糖苷酶的设计。
Glycobiology. 2016 Mar;26(3):261-9. doi: 10.1093/glycob/cwv099. Epub 2015 Nov 17.
8
Chemical Synthesis of Human Milk Oligosaccharides: para-Lacto-N-hexaose and para-Lacto-N-neohexaose.人乳寡糖的化学合成：副乳糖基六糖和副乳糖基新六糖。
Chemistry. 2023 Nov 16;29(64):e202302288. doi: 10.1002/chem.202302288. Epub 2023 Oct 6.
9
Chemical characterization of the oligosaccharides in milk of high Arctic harbour seal (Phoca vitulina vitulina).北极高纬度地区港海豹（Phoca vitulina vitulina）乳汁中寡糖的化学特征分析
Comp Biochem Physiol A Mol Integr Physiol. 2003 Aug;135(4):549-63. doi: 10.1016/s1095-6433(03)00130-2.
10
Structural determination of novel lacto-N-decaose and its monofucosylated analogue from human milk by electrospray tandem mass spectrometry and 1H NMR spectroscopy.通过电喷雾串联质谱法和¹H核磁共振光谱法测定人乳中新型乳糖-N-十糖及其单岩藻糖基化类似物的结构
Arch Biochem Biophys. 2005 Feb 1;434(1):116-27. doi: 10.1016/j.abb.2004.09.035.
引用本文的文献
1
Glycosyltransferases: glycoengineers in human milk oligosaccharide synthesis and manufacturing.糖基转移酶：人乳寡糖合成与制造中的糖基工程酶
Front Mol Biosci. 2025 Apr 30;12:1587602. doi: 10.3389/fmolb.2025.1587602. eCollection 2025.
2
Chemical Synthesis of Two Fucosylated Human Milk Oligosaccharides: 3-Fucosyllactose and Lacto-N-fucopentaose V.两种岩藻糖基化人乳寡糖的化学合成：3-岩藻糖基乳糖和乳糖-N-岩藻五糖V。
Chemistry. 2025 Jun 6;31(32):e202500754. doi: 10.1002/chem.202500754. Epub 2025 May 6.
3
Recent advances in the science of human milk oligosaccharides.人乳寡糖科学的最新进展
BBA Adv. 2025 Jan 24;7:100136. doi: 10.1016/j.bbadva.2024.100136. eCollection 2025.
4
Synthesis of 2-Amino-2-deoxy Sugars via Boron-Catalyzed Coupling of Glycosyl Fluorides and Silyl Ether Acceptors.通过硼催化糖基氟化物与硅醚受体的偶联反应合成2-氨基-2-脱氧糖
Org Lett. 2024 Sep 6;26(35):7474-7478. doi: 10.1021/acs.orglett.4c02888. Epub 2024 Aug 26.
5
Prebiotics in New-Born and Children's Health.新生儿及儿童健康中的益生元
Microorganisms. 2023 Sep 29;11(10):2453. doi: 10.3390/microorganisms11102453.
6
Chemical Synthesis of Human Milk Oligosaccharides: para-Lacto-N-hexaose and para-Lacto-N-neohexaose.人乳寡糖的化学合成：副乳糖基六糖和副乳糖基新六糖。
Chemistry. 2023 Nov 16;29(64):e202302288. doi: 10.1002/chem.202302288. Epub 2023 Oct 6.
7
Chemoenzymatic Synthesis of Asymmetrically Branched Human Milk Oligosaccharide Lacto--Hexaose.不对称支链人乳寡糖乳糖-N-己糖的化学酶法合成
Front Chem. 2022 May 31;10:905105. doi: 10.3389/fchem.2022.905105. eCollection 2022.
8
Substrate and Process Engineering for Biocatalytic Synthesis and Facile Purification of Human Milk Oligosaccharides.生物催化合成及简易人乳寡糖纯化的基质和过程工程。
ChemSusChem. 2022 May 6;15(9):e202102539. doi: 10.1002/cssc.202102539. Epub 2022 Feb 18.
9
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.
10
Like mother, like microbe: human milk oligosaccharide mediated microbiome symbiosis.像母亲一样，像微生物一样：人乳寡糖介导的微生物组共生。
Biochem Soc Trans. 2020 Jun 30;48(3):1139-1151. doi: 10.1042/BST20191144.
本文引用的文献
1
Chemical Synthesis of Human Milk Oligosaccharides: Lacto--hexaose Galβ1→3GlcNAcβ1→3 [Galβ1→4GlcNAcβ1→6] Galβ1→4Glc.人乳寡糖的化学合成：乳六糖 Galβ1→3GlcNAcβ1→3[Galβ1→4GlcNAcβ1→6]Galβ1→4Glc。
J Org Chem. 2019 Dec 20;84(24):16192-16198. doi: 10.1021/acs.joc.9b02701. Epub 2019 Dec 5.
2
The chemical synthesis of human milk oligosaccharides: Lacto-N-tetraose (Galβ1→3GlcNAcβ1→3Galβ1→4Glc).人乳寡糖的化学合成：乳-N-四糖（半乳糖β1→3-N-乙酰氨基葡萄糖β1→3-半乳糖β1→4-葡萄糖）。
Carbohydr Res. 2019 Dec 1;486:107824. doi: 10.1016/j.carres.2019.107824. Epub 2019 Sep 25.
3
The chemical synthesis of human milk oligosaccharides: Lacto-N-neotetraose (Galβ1→4GlcNAcβ1→3Galβ1→4Glc).人乳寡糖的化学合成：乳-N-新四糖（Galβ1→4GlcNAcβ1→3Galβ1→4Glc）。
Carbohydr Res. 2019 Sep 1;483:107743. doi: 10.1016/j.carres.2019.107743. Epub 2019 Jul 11.
4
Human milk oligosaccharides, milk microbiome and infant gut microbiome modulate neonatal rotavirus infection.人乳低聚糖、牛奶微生物组和婴儿肠道微生物组调节新生儿轮状病毒感染。
Nat Commun. 2018 Nov 27;9(1):5010. doi: 10.1038/s41467-018-07476-4.
5
Human Milk Nutrient Composition in the United States: Current Knowledge, Challenges, and Research Needs.美国母乳的营养成分：当前认知、挑战及研究需求
Curr Dev Nutr. 2018 May 31;2(7):nzy025. doi: 10.1093/cdn/nzy025. eCollection 2018 Jul.
6
The Human Milk Glycome as a Defense Against Infectious Diseases: Rationale, Challenges, and Opportunities.人乳糖组作为抵御传染病的防线：原理、挑战与机遇
ACS Infect Dis. 2018 Feb 9;4(2):77-83. doi: 10.1021/acsinfecdis.7b00209. Epub 2017 Nov 15.
7
Synthesis of asymmetrical multiantennary human milk oligosaccharides.不对称型多天线人乳寡糖的合成。
Proc Natl Acad Sci U S A. 2017 Jul 3;114(27):6954-6959. doi: 10.1073/pnas.1701785114. Epub 2017 Jun 19.
8
Chemoenzymatic Synthesis of a Library of Human Milk Oligosaccharides.酶化学合成人乳寡糖库。
J Org Chem. 2016 Jul 15;81(14):5851-65. doi: 10.1021/acs.joc.6b00478. Epub 2016 Jun 29.
9
A multifunctional anomeric linker for the chemoenzymatic synthesis of complex oligosaccharides.一种用于复杂寡糖化学酶促合成的多功能异头连接子。
Chem Commun (Camb). 2014 Jul 11;50(54):7132-5. doi: 10.1039/c4cc02222j.
10
Advances in analysis of human milk oligosaccharides.人乳寡糖分析的研究进展。
Adv Nutr. 2012 May 1;3(3):406S-14S. doi: 10.3945/an.112.001883.
Zotero 插件