CAS: 496-93-5; (S)-2-Amino-4-(Aminooxy)Butanoic Acid

该化合物是天然产生的氨酸衍生物,主要见于某些植物,特别是豆类种子,被归类为非蛋白性氨基酸,意思是翻译过程中未将其纳入蛋白质.L-Canaline的特点是其独特的结构,包括一个氨基组,一个碳箱基组和一个含有氮原子的侧链,有助于其基本特性.该化合物在生理pH中呈现一种zwitritic 形态,允许其参与各种生物化学互动.L-Canaline因其潜在的生物活动,包括抗微生物学和抗氧化性特性,而引起了兴趣.此外,它可能在植物防御机制中发挥作用.然而,它的确切生理功能和生物系统的行动机制仍在调查之中.与许多氨基酸一样,L-Canaline的水溶性及其再活性可以因环境条件而有所变化,使其成为植物生物化学和药学研究的主体.

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CAS号92117-88-9 ethyl N-[2-(2,5... | CAS号15985-58-7 Nα-Benzoyl-Nγ-d... | CAS号1192-69-4 DL-CYCLOHOMOSERINE | CAS号6169-65-9 2-[N-(benzenesu... | CAS号7664-41-7 氨

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    📜L-刀豆氨酸置于arginase [ec 3.5.3.1],水体系中,化学反应生成 6-硝基-2-氨苯酚-4-磺酸
    参考文献:Structure−activity Studies Of L-Canaline-Mediated Inhibition Of Porcine Alanine Aminotransferase
    标题:Structure−activity Studies Of L-Canaline-Mediated Inhibition Of Porcine Alanine Aminotransferase
    摘要:L-Canaline [l-2-Amino-4-(Aminooxy)Butanoic Acid] (L-Can) And A Family Of Eleven Structurally Related Analogs Were Synthesized And Evaluated For Their Inhibitory Effect On Plp-Dependent Alanine Aminotransferase (Alaat) (Ec 2.6.1.2) Obtained From Porcine Heart. These Congeners Were Selected To Determine The Stereochemical,Aliphatic Chain Length,And Aminooxy Substitutional Effects On L-Can-Mediated Inhibition Of Alaat Activity. L-Can Was The Most Effective Inhibitor Of The Tested Compounds; 10(-7) M L-Can Elicited A 55% Reduction In Alaat Activity After A 5 Min Exposure. This Deleterious Effect Results From The Ability Of L-Can To React Avidly With The Plp Moiety Of The Enzyme To Form A Stable,L-Can-Plp Oxime. In Contrast,The Methyl And Ethyl Esters Of L-Can Reduced Alaat Activity By Only 8% And 6%,Respectively. While All Of The L-Enantiomeric Forms Of The Tested Compound Were More Potent Alaat Inhibitors Than Their Corresponding D-Stereoisomers,The D-Enantiomers,Particularly D-Canaline,Were Active. Chain Shortening Or Lengthening Dramatically Curtailed L-Can-Mediated Loss In Alaat Activity,But The Replacement Of The Cr-Amino Group With A Hydrogen Was Of Little Consequence In This Regard. Alaat Was Treated With L-Can In The Presence Of Free Plp To Assess Plp Capacity To Protect Alaat Against 10(-7) M L-Can-Dependent Inactivation. L-Can Retained Approximately Two-Thirds Of Its Inhibitory Ability In The Presence Of Equimolar Plp,But Alaat Inhibition Was Reduced 90% By A 10-Fold Excess Of Plp Over L-Can.
    DOI:10.1021/tx9600199

    海关参考信息

    专利信息


    专利号:US-2004053999-A1
    优先权日:1997-09-17
    标题 :Novel compounds and methods for synthesis and therapy
    发明人:BISCHOFBERGER NORBERT W; DAHL TERRENCE C; HITCHCOCK MICHAEL J M; KIM CHOUNG U; LEW WILLARD; LIU HONGTAO; MILLS ROGER G; WILLIAMS MATTHEW A
    摘要:Novel compounds are described. The compounds generally comprise an acidic group, a basic group, a substituted amino or N-acyl and a group having an optionally hydroxylated alkane moiety. Pharmaceutical compositions comprising the inhibitors of the invention are also described. Methods of inhibiting neuraminidase in samples suspected of containing neuraminidase are also described. Antigenic materials, polymers, antibodies, conjugates of the compounds of the invention with labels, and assay methods for detecting neuraminidase activity are also described.

    专利号:US-6225341-B1
    优先权日:1995-02-27
    标 题:Compounds and methods for synthesis and therapy
    发明人:BISCHOFBERGER NORBERT W; KIM CHOUNG U; LEW WILLARD; LIU HONGTAO; WILLIAMS MATTHEW A
    权利人:GILEAD SCIENCES INC
    摘要:Novel compounds are described. The compounds generally comprise an acidic group, a basic group, a substituted amino or N-acyl and a group having an optionally hydroxylated alkane moiety. Pharmaceutical compositions comprising the inhibitors of the invention are also described. Methods of inhibiting neuraminidase in samples suspected of containing neuraminidase are also described. Antigenic materials, polymers, antibodies, conjugates of the compounds of the invention with labels, and assay methods for detecting neuraminidase activity are also described.

    专利号:US-2003232820-A1
    优先权日:2001-08-29
    标题:Method for synthesizing oxazinones
    发明人:WOLFE SAUL; WILSON MARIE-CLAIRE; CHENG MING-HUEI
    摘要:New methods and intermediates are discussed for the stereospecific synthesis of oxazinone compounds.

    专利号:US-3957760-A
    优先权日:1970-12-16
    标 题:Amino acid derivatives
    发明人:BODANSZKY MIKLOS
    权利人:SQUIBB & SONS INC
    摘要:New lactone intermediates useful in the synthesis of peptides are prepared by reacting an α-amino acid with an active carbonyl compound which forms a Schiff's base. The latter is treated with a condensing agent so that cyclization occurs and a lactone is formed from which a peptide may be produced by reaction with an amino acid ester and removal of the protecting groups.

    专利号:US-5449688-A
    优先权日:1993-03-30
    标 题:Method of treating chronic inflammatory diseases
    发明人:WAHL SHARON M; ALLEN JANICE B; MCCARTNEY-FRANCIS NANCY L
    权利人:US ARMY
    摘要:The present invention provides a method for treating chronic inflammatory conditions, including autoimmune diseases by administering an effective amount of an agent, such as a nitric oxide synthase inhibitor, a nitric oxide scavenger, or an inhibitor of tetrahydrobiopterin synthesis, to decrease the amount of nitric oxide present at the site of inflammation.

    专利号:EP-0703732-B1
    优先权日:1993-06-17
    标 题:Food and/or pharmaceutical composition having a low polyamine content
    发明人:MOULINOUX JACQUES-PHILIPPE; QUEMENER VERONIQUE; JAUSSAN VERONIQUE
    权利人:UNIV RENNES
    摘要:An esculent composition consisting of a nutrient mixture having a low polyamine content, containing less than 50 picomoles/g of putrescine, spermidine, spermine and cadaverine, and containing (expressed in dry weight % on the basis of the overall dry weight) 10-35 % lipids, 8-30 % proteins, 35-80 % carbohydrates, and up to 10 % a mixture of vitamins, minerals and electrolytes. Said composition is advantageously enriched with or administered in combination with at least one intracellular polyamine synthesis inhibitor in an amount of no more then 15 wt % on the basis of the overall dry weight.

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    主要参考文献

    1. Bolkenius, F.N., Knödgen, B., and Seiler, N. DL-Canaline and 5-fluoromethylornithine. Comparison of two inactivators of ornithine aminotransferase. Biochem. J. 268, 409-414 (1990). 2. Heilbronn, J., Wilson, J., and Berger, B.J. Tyrosine aminotransferase catalyzes the final step of methionine recycling in Klebsiella pneumoniae. J. Bacteriol. 181(6), 1739-1747 (1999). 3. Worthen, D.R., Ratliff, D.K., Rosenthal, G.A., et al. Structure-activity studies of L-canaline-mediated inhibition of porcinealanine aminotransferase. Chem. Res. Toxicol. 9(8), 1293-1297 (1996). 4. Rosenthal, G.A. L-Canavanine Transport and Utilization in Developing Jack Bean, Canavalia ensiformis (L.) DC. [Leguminosae]. Plant Physiol. 69, 1066-1069 (1982). 5. Berger, B.J. Antimalarial activities of aminooxy compounds. Antimicrob. Agents Chemother. 44(9), 2540-2542 (2000).

    合成参考文献


    参考文献:10.1007/bf00143389
    摘要:Schenkel E, Dubois JG, Helson-Cambier M, Hanocq M. Cytotoxicity of polyamines to Amoeba proteus: role of polyamine oxidase. Cell Biol Toxicol. 1996 Feb;12(1):1–9. doi: 10.1007/bf00143389.
    参考文献:10.1007/bf02160392
    摘要:Knobler Y, Weiss M. A colorimetric determination of aminooxy acids. Cellular and Molecular Life Sciences. 1958 Sep;14(9):332. doi: 10.1007/bf02160392.
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