CAS: 2491-15-8; N-Formylglycine

该化合物是一种经过修改的氨基酸衍生物,其中以气态体组取代了盐碱的氢氧基,这种结构改变具有独特的反应性,使其成为有机合成和生物催化的宝贵中间体,是生产peptiomimicics和酶抑制剂的主要前体,特别是在涉及硫脂酶和其他水溶酶的研究中,在生理条件下的稳定性和与生物系统的兼容性使其适合进行生化研究和药物应用. N-Formylglycine还被用于制造酶机制,并设计有针对性的治疗方法,因为其有能力在酶反应中模拟转型状态.

结构式图片

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CAS号64-18-6 甲酸 | CAS号56-40-6 甘氨酸 | CAS号51354-16-6 [N-formyl(O-ben... | CAS号623-33-6 甘氨酸乙酯盐酸盐 | CAS号149-73-5 原甲酸三甲酯 | CAS号298-12-4 乙醛酸 | CAS号77287-34-4 甲亚胺酸 | CAS号2258-42-6 甲乙酐 | CAS号7750-46-1 Formylglycin-(2... | CAS号3154-51-6 N-甲酰基甘氨酸乙酯 | CAS号2999-46-4 异氰基乙酸乙酯 | CAS号56-40-6 甘氨酸 | CAS号497-24-5 噁唑-5-酮

合成工艺路线路线简述

    Benzyl 2-Formamidoacetate置于palladium 10% On Activated Carbon,氢气体系中,用 四氢呋喃 用作溶剂,以92%的收率获得n-甲酰甘氨酸
    参考文献:通过passerini 反应合成 No-Nsaid 树枝状前药:设计树枝状药物偶联物的新方法
    标题:通过passerini 反应合成 No-Nsaid 树枝状前药:设计树枝状药物偶联物的新方法
    摘要:我们报告了在一个锅中通过 Passerini 反应合成一类新型树突状前药.这种树枝状聚合物的特点是同时附着传统的非甾体抗炎药 (Nsaid)(如布洛芬和阿司匹林)和一氧化氮 (No) 释放部分(如有机硝酸盐)到它们的表面,因此被认为是释放 No 的 Nsaids (No-Nsaids) 的新给药系统.
    Doi:10.3184/174751913X13602469418189

    海关参考信息

    专利信息


    专利号:US-7160517-B2
    优先权日:2000-08-18
    标题 :Apparatus and methods for the automated synthesis of oligosaccharides
    发明人:SEEBERGER PETER H; PLANTE OBADIAH J
    权利人:MASSACHUSETTS INST OF TECHNOLG
    摘要:One aspect of the present invention relates to an apparatus for the efficient synthesis of oligosaccharides on a solid support, e.g., formed by subunit addition to terminal subunits immobilized on solid-phase particles. In certain embodiments, the apparatus of the present invention is used in combinatorial methods, e.g., as described herein, of synthesizing oligosaccharides.

    专利号:WO-2007003236-A1
    优先权日:2005-06-30
    标 题:Process for synthesis of complex 2-deoxy-2-iodo pyranosides of high purity, particularly suitable for manufacturing pharmaceutically pure annamycin
    发明人:SZEJA WIESLAW; GRYNKIEWICZ GRZEGORZ; FOKT IZABELA
    权利人:ZACLAD BADAWCZO PROD SYNTEX; SZEJA WIESLAW; GRYNKIEWICZ GRZEGORZ; FOKT IZABELA
    摘要:The method according to the invention comprises using as glycosyl donors high purity 2- deoxy-2-iodo derivatives of sugars of a defined configuration of C-2 carbon with O-alkyl, S- alkyl, O-aryl, S-aryl, O-heteroaryl, S-heteroaryl, O-acyl, O-silyl, O-N-imido, O-P- (phosphino, phosphono, thiophosphono, selenophosphono) groups at the anomeric position, and subjecting them to a condensation reaction with a compound containing a hydroxyl group or a protected hydroxyl group in the presence of electrophilic reagents, followed by deprotection and isolation of a pharmaceutically pure product. The objective of the present invention is to provide a method for preparing complex glycosides by coupling cyclic multifunctional compounds containing hydroxyl functional groups (glycosyl acceptors, including aglycones of natural origin which are known as constituents of active pharmaceutical ingredients) with diastereoisomerically pure 2-deoxy-2-halopyranosyl derivatives containing anomeric substituent capable of exchange under glycosidating conditions, for example by virtue of activation with electrophilic agents. This method substantially simplifies the synthesis of Annamycin. The present invention relies on a regio- and stereoselective reaction of cohalogenating 1,2- unsaturated sugars in the presence of hydroxyl group containing compounds, such as: water, alcohols, phenols, carboxylic acids, silanols, phosphinic acids, phosphoric acids, thiophosphoric acids, selenophosphoric acids, followed by separation of the product with proper C-2 carbon configuration required for the synthesis. As the separation of stereoisomers is carried out at the stage of obtaining a relatively inexpensive intermediate in the form of glycosyl donor, the method of the invention substantially reduces the cost of Annamycin manufacture. Other advantages of the synthesis process of the invention consist in the reduction of the number of stages of the antibiotic manufacture process and in yield increase of the final product.

    专利号:WO-9407900-A1
    优先权日:1992-09-25
    标 题 :Synthesis of n-glycosylated compounds with the use of a mild, iodine-catalyzed reaction
    发明人:KOREEDA MASATO; HOUSTON TODD A
    权利人:UNIV MICHIGAN
    摘要:The invention concerns N-glycosylated derivatives of nitrogen nucleophile compounds. The invention also concerns a mild, cost effective, stereoselective, regioselective, and generally applicable method for the preparation of N-glycosides by N-glycosylation of azide and amide nucleophile compounds. The method employs iodine in a catalytic amount that uniquely does not pose an environmental hazard. The invention provides efficient access to key intermediates for the synthesis inter alia of analogs of AZT and DDI and for the synthesis of conventional N-nucleoside antibiotic drugs and their novel N-glycosylated analogs.

    专利号:US-6069250-A
    优先权日:1995-12-14
    标 题 :Method and compositions for the synthesis of dioxolane nucleosides with β-configuration
    发明人:MANSOUR TAREK; CIMPOIA ALEX; BEDNARSKI KRZYSZTOF
    权利人:IAF BIOCHEM INT
    摘要:The present invention relates to methods and compositions for preparing biologically important nucleoside analogues containing 1,3-dioxolane sugar rings. In particular, this invention relates to the stereoselective synthesis of the beta (cis) isomer by glycosylating the base with an intermediate of formula (II) below a temperature of about -10 DEG C. wherein R1 and L are as defined herein.

    专利号:US-4242256-A
    优先权日:1977-03-15
    标 题 :Synthesis of peptide analogues
    发明人:SHARPE ROBERT; SZELKE MICHAEL
    权利人:SHARPE ROBERT; SZELKE MICHAEL
    摘要:Compounds being analogues of a dipeptide in which the nitrogen atom of the linking amide group of the dipeptide is replaced by trivalent group ##STR1## and in which, optionally, the carbonyl function of this linking group is replaced by the divalent group --CH 2 -- are of value in the synthesis of isosterically modified peptides.

    专利号:US-9512162-B2
    优先权日:2012-07-31
    标题 :Synthesis of deuterated ribo nucleosides, N-protected phosphoramidites and oligonucleotides
    发明人:SRIVASTAVA SURESH C; YASKO AMY
    权利人:ASED LLC
    摘要:The present invention is directed towards the synthesis of high purity deuterated sugars, deuterated phosphoramidites, deuterated nucleobases, deuterated nucleosides, deuterated oligonucleotides, and deuterated RNA's of defined sequences which can exhibit biochemically useful and biologically valuable properties, thus having potential for therapeutic uses.
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    主要参考文献

    [参考文献]: Annette Sievers, Et Al. The Ribosome As An Entropy Trap. Proc Natl Acad Sci U S A. 2004 May 25;101(21):7897-901.
    [参考文献]: Brian L Carlson, Et Al. Function And Structure Of A Prokaryotic Formylglycine-Generating Enzyme. J Biol Chem. 2008 Jul 18;283(29):20117-25.
    [参考文献]: Einar Sagstuen, Et Al. Electron Transfer In Amino Acid.Nucleic Acid Base Complexes: Epr, Endor, And Dft Study Of X-Irradiated N-Formylglycine.Cytosine Complex Crystals. J Phys Chem A. 2006 Jul 20;110(28):8653-62.
    [参考文献]: Eva C Ennemann, Et Al. Proprotein Convertases Process And Thereby Inactivate Formylglycine-Generating Enzyme. J Biol Chem. 2013 Feb 22;288(8):5828-39.
    [参考文献]: Jason S Rush, Et Al. New Aldehyde Tag Sequences Identified By Screening Formylglycine Generating Enzymes In Vitro And In Vivo. J Am Chem Soc. 2008 Sep 17;130(37):12240-1.

    合成参考文献


    参考文献:10.1007/s00253-010-2455-0
    摘要:Fetzner S, Steiner RA. Cofactor-independent oxidases and oxygenases. Applied Microbiology and Biotechnology. 2010 Feb 16;86(3):791–804. doi: 10.1007/s00253-010-2455-0.
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