CAS: 2438-80-4; (2S,3R,4R,5S)-2,3,4,5-Tetrahydroxyhexanal

该化合物是天然生成的脱氧exose糖,具体而言,Fucose的L-enantomer,其分子式为C6H12O5. 它是甘蓝蛋白,甘蓝脂和寡头沙律的关键成分,在细胞识别和免疫反应调节方面发挥着关键作用. (-)-Fucose在遗传生物学研究中被广泛使用,特别是在涉及细胞表面相互作用,细菌粘合和炎症发反应过程的研究中被广泛使用.其高纯度和定义明确的结构使其对酶和合成应用具有价值.该化合物还被用于开发针对烟花代代生物路径的诊断工具和治疗剂.稳定和可复制性确保其在实验和工业用途中的可靠性.

结构式图片

相似化合物

3615-37-0 10030-85-0 3615-41-6

欧盟法规

ECHA物质C&L通报REACH预注册

上下游产品

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合成工艺路线路线简述

  • 合成目标产物 L-Fucose 主要起始原料 Acrylamide
  • (文献来源)合成步骤主要原料 Acrylamide
(4S,5R)-2,2-Dimethyl-5-((4R,5S)-2,2,5-Trimethyl-1,3-Dioxolan-4-yl)-1,3-Dioxolane-4-Carbaldehyde置于dowex (50W X8,H+ Form)体系中,用 水 用作溶剂,化学反应 24.0H,以74%的收率获得l(-)岩藻糖
参考文献:L-Fucose From Vitamin C With Only Acetonide Protection
标题:L-Fucose From Vitamin C With Only Acetonide Protection
摘要:Addition Of Human Milk Oligosaccharides (Hmo) To Baby Foods May Protect Infants From Disease. As Many Simple Hmos Are Fucosylated This Is Likely To Increase The Demand For L-Fucose As A Synthetic Building Block. Any Chemical Synthesis Must Be Cheap To Compete With A Biotechnological Process. Acetonide Is The Only Protecting Group We Have Used In This New Synthesis Of L-Fucose From Vitamin C In 27% Overall Yield (Purification By Recrystallization; No Chromatography Required In The Entire Sequence).
Doi:10.1021/ol502733X

海关参考信息

专利信息


专利号:US-9512420-B2
优先权日:2013-10-16
标题:Use of N-acetylneuraminic acid aldolase in catalytic synthesis of N-acetylneuraminic acid
发明人:XIE JINGJING; JI WENYAN; YING HANJIE; Sun wujin; GUO TING; CHEN YONG; CHEN XIAOCHUN; WU JINGLAN
权利人:NANJING UNIV OF TECH; NANJING UNIVERSITY OF TECHNOLOGY
摘要:It discloses a use of N-acetylneuraminic acid aldolase with an amino acid sequence as shown in SEQ ID NO: 2 in catalytic synthesis of N-acetylneuraminic acid. The preparation of N-acetylneuraminic acid is to use the N-acetylneuraminic acid aldolase with the amino acid sequence as shown in SEQ ID NO: 2 as a catalyst, and N-acetylmannosamine and pyruvic acid as substrates.

专利号:WO-2010103857-A1
优先权日:2009-03-12
标 题 :Method for solid-phase synthesis of glycopeptide using silicon-containing protecting group and synthesis device
发明人:NISHIMURA SHIN-ICHIRO; SHIMAWAKI KEN
权利人:UNIV HOKKAIDO NAT UNIV CORP; NISHIMURA SHIN-ICHIRO; SHIMAWAKI KEN
摘要:Disclosed are a novel method for the synthesis of a glycopeptide by which glycopeptides of various types can be deprotected and excised from a resin, each under weakly acidic to weakly basic conditions, without causing the problems of the epimerization of an amino acid at the a-position and the ß-elimination of a sugar residue; a synthesis device therefor; and a synthesis intermediate to be used in synthesizing a glycopeptide. Specifically disclosed are a method for the solid-phase synthesis of a glycopeptide which comprises a step for obtaining a glycopeptide derivative wherein the N-terminus is protected, the C-terminus is immobilized to a solid phase via a silicon linker, and a reactive group carried by a sugar residue and a reactive group carried by an amino acid side chain constituting a peptide are protected by silicon-containing groups, and a step for obtaining the glycopeptide by deprotecting said glycopeptide derivative and releasing the same from the solid phase by treating the glycopeptide derivative with an agent for removing the silicon-containing groups and the silicon linker; a synthesis intermediate to be used in the step for obtaining the glycopeptide derivative in the aforesaid method; and a device for the solid-phase synthesis of a glycopeptide.

专利号:US-2004266699-A1
优先权日:2001-10-04
标 题 :Flavonoid compounds capable of modifying the dynamic and/or physical state of biological membranes and to stimulate the endogenous synthesis of stress proteins in eukaryotic cells, relative synthesis and their use
发明人:PORTA AMALIA
摘要:The invention relates to flavonoids compounds of formula (I) and (II) capable of modifying the dynamic and/or physical state of biological membranes and to stimulate the endogenous synthesis of stress proteins in eukaryotic cells. Such compounds are molecules of plant origin or synthetic. The invention also describes a method to identify, purify and chemically synthesize such flavonoid compounds and test their efficacy through their capacity to stimulate the transcription of stress genes and as a consequence, to interact with biological membranes with alteration of their relative physical state. Such compounds and corresponding pharmaceutically acceptable derivatives and/or salts have applications in the areas of pharmaceuticals, more specifically in cosmetics and dermatology, for all those afections related to an alteration of the expression of stress genes.

专利号:US-2022395800-A1
优先权日:2019-11-04
标题:Device for automated synthesis of oligo- and polysaccharides
发明人:SEEBERGER PETER H; DANGLAD FLORES JOSE; LE MAI HOANG KIM; PARDO VARGAS ALONSO; SLETTEN ERIC; SALWICZEK MARIO
权利人:MAX PLANCK GESELLSCHAT ZU RFERDERUNG DER WSS E V; GlycoUniverse GmbH & Co KG&A
摘要:The present invention generally relates to automated synthesis technology, and more particularly, to a device and method for automated synthesis of oligo- and polysaccharides on a solid support. In particular the present invention relates to a device for automated synthesis of oligo- and polysaccharides on a solid support comprising a reaction vessel, a reagent storing component, a reagent delivery system, a cooling device for cooling reaction vessel, and a pre-cooling device for pre-cooling the reagents to be supplied.

专利号:WO-9423054-A1
优先权日:1993-04-05
标 题:Synthesis of tetrasaccharide
发明人:NILSSON KURT
权利人:PROCUR AB; NILSSON KURT
摘要:The present invention relates to a method for synthesis of a tetrasaccharide or a derivative thereof, which includes the initial synthesis with two different glycosidases of two disaccharides, or derivatives thereof, which after modification are used as donor and acceptor in chemical synthesis of the tetrasaccharide or its derivative.

专利号:US-10751419-B2
优先权日:2014-05-01
标题:Method for synthesis of reactive conjugate clusters
发明人:MIGAWA MICHAEL T; YU JINGHUA; WAN W BRAD; PATEL SAYTEN P; VASQUEZ GUILLERMO; KINBERGER GARTH A; PRAKASH THAZHA P; SETH PUNIT P; SWAYZE ERIC E
权利人:IONIS PHARMACEUTICALS INC
摘要:Provided herein are improved methods for the synthesis of reactive conjugate clusters and intermediates used in such methods. In particular, improvements are provided that enhance the synthesis of reactive conjugate clusters by reducing the number of synthetic steps required. The reactive conjugate clusters prepared using the improved methods don't include any transacylation impurities that are formed using existing methods. The improved methods also provide an increase in overall yield and a cost benefit over existing methods.
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1: Shoemaker CA, LaFrentz BR, Peatman E, Beck BH. Influence of native catfish mucus on Flavobacterium columnare growth and proteolytic activity. J Fish Dis. 2018 Jun 11. doi: 10.1111/jfd.12833. [Epub ahead of print] doi: 10.1016/j.carres.2018.05.008. [Epub ahead of print] doi: 10.1016/j.carres.2018.05.005. Epub 2018 May 16. doi: 10.1021/acs.jnatprod.8b00212. Epub 2018 May 16. doi: 10.1111/1750-3841.14125. Epub 2018 Apr 6. doi: 10.1016/j.tice.2018.03.006. Epub 2018 Mar 12. doi: 10.1016/j.carres.2018.02.013. Epub 2018 Mar 6. doi: 10.1016/j.clim.2018.03.017. Epub 2018 Mar 30.
11: Perrella NN, Fuzita FJ, Moreti R, Verhaert PDEM, Lopes AR. First characterization of fucosidases in spiders. Arch Insect Biochem Physiol. 2018 Jul;98(3):e21462. doi: 10.1002/arch.21462. Epub 2018 Mar 30. doi: 10.1556/018.68.2018.1.9. doi: 10.1016/j.jfda.2017.07.006. Epub 2017 Aug 18. doi: 10.1021/acs.joc.8b00008. Epub 2018 Mar 13. doi: 10.1016/j.carbpol.2018.01.029. Epub 2018 Jan 11. doi: 10.1038/s41598-018-21375-0.
17: Cattiaux L, Porkolab V, Fieschi F, Mallet JM. New branched amino acids for high affinity dendrimeric DC-SIGN ligands. Bioorg Med Chem. 2018 Mar 1;26(5):1006-1015. doi: 10.1016/j.bmc.2017.12.036. Epub 2017 Dec 26. doi: 10.1021/acsinfecdis.7b00085. Epub 2018 Feb 22.

合成参考文献


参考文献:10.3390/md9060952
摘要:Costa LS, Fidelis GP, Telles CBS, Dantas-Santos N, Camara RBG, Cordeiro SL, Costa MSSP, Almeida-Lima J, Melo-Silveira RF, Oliveira RM, Albuquerque IRL, Andrade GPV, Rocha HAO. Antioxidant and antiproliferative activities of heterofucans from the seaweed Sargassum filipendula. Mar Drugs. 2011;9(6):952–66.
参考文献:10.1073/pnas.1108455108
摘要:Ferrara C, Grau S, Jäger C, Sondermann P, Brünker P, Waldhauer I, Hennig M, Ruf A, Rufer AC, Stihle M, Umaña P, Benz J. Unique carbohydrate-carbohydrate interactions are required for high affinity binding between FcgammaRIII and antibodies lacking core fucose. Proc Natl Acad Sci U S A. 2011 Aug 02;108(31):12669–74.
参考文献:10.4103/0973-1482.82928
摘要:Parwani RN, Parwani SR. Quantitative evaluation of serum fucose in oral squamous cell carcinoma patients. J Cancer Res Ther. 2011 Apr;7(2):143–7. doi: 10.4103/0973-1482.82928.
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