2-酮基-3-脱氧-D-甘油-D-半乳糖壬酮糖酸（KDN）的实用合成。
Practical synthesis of 2-keto-3-deoxy-D-glycero-D-galactononulosonic acid (KDN).
机构信息
Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, USA.
出版信息
Org Lett. 2011 Dec 2;13(23):6288-91. doi: 10.1021/ol202773t. Epub 2011 Nov 9.
Abstract
Reaction of propargylmagnesium bromide with 2,3;5,6-di-O-isopropylidene-D-mannonolactone followed by highly stereoselective reduction of the so-formed lactol with sodium borohydride gives a syn-diol from which practical syntheses of 2-keto-3-deoxy-D-glycero-D-galactononulosonic acid (KDN) and various partially protected derivatives have been achieved all of which feature the oxidative unmasking of the α-keto acid moiety from the alkyne.
摘要
炔丙基溴化镁与 2,3;5,6-二-O-亚异丙基-D-甘露诺内酯反应，然后用硼氢化钠对所形成的内醇进行高度立体选择性还原，得到顺二醇，由此可实用合成 2-酮基-3-脱氧-D-甘油-D-半乳糖壬酮酸（KDN）和各种部分保护的衍生物，这些都具有从炔烃中氧化脱保护α-酮酸部分的特点。
相似文献
1
Practical synthesis of 2-keto-3-deoxy-D-glycero-D-galactononulosonic acid (KDN).2-酮基-3-脱氧-D-甘油-D-半乳糖壬酮糖酸（KDN）的实用合成。
Org Lett. 2011 Dec 2;13(23):6288-91. doi: 10.1021/ol202773t. Epub 2011 Nov 9.
2
Use of Phenols as Nucleophiles in the Zbiral Oxidative Deamination of -Acetyl Neuraminic Acid: Isolation and Characterization of Tricyclic 3-Keto-2-deoxy-nonulosonic Acid (KDN) Derivatives via an Intermediate Vinyl Diazonium Ion.酚类作为亲核试剂在 Zbiral 氧化脱氨反应中的应用：通过中间乙烯基重氮离子对三环 3-酮-2-脱氧壬酮糖酸（KDN）衍生物的分离和特性研究。
J Org Chem. 2019 Nov 15;84(22):14688-14700. doi: 10.1021/acs.joc.9b02279. Epub 2019 Oct 29.
3
Stereoselective synthesis of the alpha-allyl C-glycoside of 3-deoxy-D-manno-2-octulosonic acid (KDO) by use of radical chemistry.利用自由基化学方法立体选择性合成3-脱氧-D-甘露-2-辛酮糖酸（KDO）的α-烯丙基碳苷。
Acta Chem Scand (Cph). 1992 Jan;46(1):73-6. doi: 10.3891/acta.chem.scand.46-0073.
4
Effect of Protecting Groups and Activating Conditions on 3-Deoxy-d--d--2-nonulosonic Acid (Kdn) Glycosylation: Stereoselective Synthesis of α- and β-Kdn Glycosides.保护基团和活化条件对3-脱氧-D-甘露-2-壬酮糖酸（Kdn）糖基化的影响：α-和β-Kdn糖苷的立体选择性合成
Org Lett. 2025 Jan 10;27(1):303-308. doi: 10.1021/acs.orglett.4c04325. Epub 2024 Dec 20.
5
Stereoselective synthesis of alpha-keto-deoxy-D-glycero-D-galacto-nonulosonic acid glycosides by means of the 4,5-O-carbonate protecting group.通过 4,5-O-碳酸酯保护基对 alpha-酮去氧-D-甘油-D-半乳糖-壬酮糖苷进行立体选择性合成。
Angew Chem Int Ed Engl. 2010 Apr 12;49(17):3049-52. doi: 10.1002/anie.200907178.
6
Synthesis of the nucleoside analogues of 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN).3-脱氧-D-甘油-D-半乳糖-2-壬酮糖酸（KDN）核苷类似物的合成
Nucleic Acids Symp Ser. 1991(25):137-9.
7
Formal synthesis of (+)-3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) via desymmetrization by ring-closing metathesis.通过闭环复分解去对称化法对（+）-3-脱氧-D-甘油-D-半乳糖-2-壬酮糖酸（KDN）进行形式合成。
Org Lett. 2001 Jan 25;3(2):237-40. doi: 10.1021/ol006887l.
8
Biosynthesis of KDN (2-keto-3-deoxy-D-glycero-D-galacto-nononic acid). Identification and characterization of a KDN-9-phosphate synthetase activity from trout testis.KDN（2-酮基-3-脱氧-D-甘油-D-半乳糖壬糖酸）的生物合成。虹鳟鱼睾丸中KDN-9-磷酸合成酶活性的鉴定与表征。
J Biol Chem. 1999 Aug 13;274(33):22949-56. doi: 10.1074/jbc.274.33.22949.
9
Syntheses of 2-keto-3-deoxy-D-xylonate and 2-keto-3-deoxy-L-arabinonate as stereochemical probes for demonstrating the metabolic promiscuity of Sulfolobus solfataricus towards D-xylose and L-arabinose.2-酮-3-脱氧-D-木酮糖和 2-酮-3-脱氧-L-阿拉伯糖的合成作为用于展示 Sulfolobus solfataricus 对 D-木糖和 L-阿拉伯糖代谢混杂性的立体化学探针。
Chemistry. 2013 Feb 18;19(8):2895-902. doi: 10.1002/chem.201203489. Epub 2013 Jan 11.
10
Human symbiont Bacteroides thetaiotaomicron synthesizes 2-keto-3-deoxy-D-glycero-D- galacto-nononic acid (KDN).人类共生菌多形拟杆菌可合成2-酮-3-脱氧-D-甘油-D-半乳糖壬糖酸（KDN）。
Chem Biol. 2008 Sep 22;15(9):893-7. doi: 10.1016/j.chembiol.2008.08.005.
引用本文的文献
1
Sialic acids Neu5Ac and KDN in adipose tissue samples from individuals following habitual vegetarian or non-vegetarian dietary patterns.习惯性素食或非素食饮食模式个体的脂肪组织样本中的唾液酸 Neu5Ac 和 KDN。
Sci Rep. 2023 Aug 3;13(1):12593. doi: 10.1038/s41598-023-38102-z.
2
Improved synthesis and application of conjugation-amenable polyols from d-mannose.从D-甘露糖改进共轭亲和多元醇的合成与应用。
RSC Adv. 2020 Jan 23;10(7):3960-3966. doi: 10.1039/c9ra10378c. eCollection 2020 Jan 22.
3
Thermal, Spectroscopic, and Crystallographic Analysis of Mannose-Derived Linear Polyols.甘露糖衍生线性多元醇的热分析、光谱分析和晶体学分析
Cryst Growth Des. 2018 May 2;18(5):3151-3160. doi: 10.1021/acs.cgd.8b00263. Epub 2018 Apr 9.
4
A Semi-Synthetic Glycoconjugate Vaccine Candidate for Carbapenem-Resistant Klebsiella pneumoniae.一种用于治疗碳青霉烯类耐药肺炎克雷伯菌的半合成糖缀合物疫苗候选物。
Angew Chem Int Ed Engl. 2017 Nov 6;56(45):13973-13978. doi: 10.1002/anie.201700964. Epub 2017 Oct 5.
5
De novo synthesis of D- and L-fucosamine containing disaccharides.从头合成含 D-和 L-岩藻糖的二糖。
Beilstein J Org Chem. 2013;9:332-41. doi: 10.3762/bjoc.9.38. Epub 2013 Feb 14.
本文引用的文献
1
Human KDN (deaminated neuraminic acid) and its elevated expression in cancer cells: mechanism and significance.人KDN（脱氨神经氨酸）及其在癌细胞中的高表达：机制与意义
Adv Exp Med Biol. 2011;705:669-78. doi: 10.1007/978-1-4419-7877-6_35.
2
Chemoenzymatic synthesis of differentially protected 3-deoxysugars.酶促化学合成差向保护的 3-脱氧糖。
Nat Chem. 2010 Feb;2(2):102-5. doi: 10.1038/nchem.504. Epub 2010 Jan 17.
3
Stereoselective synthesis of alpha-keto-deoxy-D-glycero-D-galacto-nonulosonic acid glycosides by means of the 4,5-O-carbonate protecting group.通过 4,5-O-碳酸酯保护基对 alpha-酮去氧-D-甘油-D-半乳糖-壬酮糖苷进行立体选择性合成。
Angew Chem Int Ed Engl. 2010 Apr 12;49(17):3049-52. doi: 10.1002/anie.200907178.
4
KDN (deaminated neuraminic acid): dreamful past and exciting future of the newest member of the sialic acid family.KDN（脱氨神经氨酸）：唾液酸家族最新成员的梦幻往昔与激动人心的未来。
Glycoconj J. 2006 Jul;23(5-6):277-90. doi: 10.1007/s10719-006-6484-y.
5
Synthesis of the sialic acid (-)-KDN and certain epimers from (-)-3-dehydroshikimic acid or (-)-quinic acid.从（-）-3-脱氢莽草酸或（-）-奎尼酸合成唾液酸（-）-KDN及某些差向异构体。
Org Lett. 2004 Aug 5;6(16):2737-40. doi: 10.1021/ol049048y.
6
Synthesis and elaboration of functionalised carbohydrate-derived spiroketals.功能化碳水化合物衍生的螺缩酮的合成与阐述
Org Biomol Chem. 2004 May 7;2(9):1395-403. doi: 10.1039/b401699h. Epub 2004 Apr 5.
7
Synthesis of sialic acids via desymmetrization by ring-closing metathesis.通过闭环复分解去对称化合成唾液酸。
J Org Chem. 2002 Nov 29;67(24):8489-99. doi: 10.1021/jo0263014.
8
A new synthesis of Neu5Ac from D-glucono-delta-lactone.一种从D-葡萄糖酸-δ-内酯合成唾液酸（Neu5Ac）的新方法。
J Org Chem. 2002 Sep 20;67(19):6758-63. doi: 10.1021/jo026056o.
9
Chemical diversity in the sialic acids and related alpha-keto acids: an evolutionary perspective.唾液酸及相关α-酮酸中的化学多样性：进化视角
Chem Rev. 2002 Feb;102(2):439-69. doi: 10.1021/cr000407m.
Zotero 插件