CAS: 4549-02-4; Maculosin

该化合物是一种由氨基酸分泌和铁合氨酸分泌构成的环状二极酯,该化合物具有独特的环状结构,影响其生化特性和相互作用.Cyclo(L-Pro-L-Tyr)具有peptides的典型特征,包括形成氢联结和从事各种可影响其溶解性和稳定性的分子间相互作用的能力.Proline残留物的存在会助长peptide骨架的僵硬性,而带有芳香环的苯乙烯侧链则可以参与欧元的堆叠相互作用和氢结,增强它潜在的生物活动.该化合物可能表现出抗氧化性特性,因为有抗腐蚀性细胞,它能够产生碳凝结自由的基.此外,环球(L-p-L-Tyr)的存在可能会对药基的基化学和药物设计产生影响,特别是对其具体的治疗活动进行深入了解.

结构式图片

物理性质

MSDS等安全信息

欧盟法规

C&L通报

上下游产品

(tert-butoxycarbonyl)-L-tyrosyl-L-proline B°C-Tyr-OH L-prolinamide B°C-Tyr-Pro-OBzlL-tyrosine L-prolineL-proline 4-(((3S,8aS)-1,4-dioxo°Ctahydropyrrolo[1,2-a]pyrazin-3-yl)methyl)phenyl trifluoromethanesulfonate (3S,8aR)-3-(4-hydroxybenzyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione

合成工艺路线路线简述

    📜在 盐酸,Sodium Hydroxide体系中,用 水,乙酸乙酯 作为反应溶剂,化学反应 1.5H,以78%的收率获得产物环(脯氨酸一酪氨酸)
    参考文献:从苏云金芽孢杆菌和内生芽孢杆菌中分离出的二酮哌嗪衍生物,通过x射线建立构型及其合成
    标题:从苏云金芽孢杆菌和内生芽孢杆菌中分离出的二酮哌嗪衍生物,通过x射线建立构型及其合成
    摘要:从苏云金芽孢杆菌菌株中已经分离出四种已知的二酮哌嗪,并且也从内生芽孢杆菌中分离出其中的两种.通过完整的光谱学阐明了它们的结构,并且通过x射线分析确定了其中三个的构型.从两个菌株分离的双西哌嗪环-(1-脯氨酸-1-酪氨酸)是多晶型的,显示出不同的物理性质.只需两个简单步骤即可成功实现合成.他们针对某些革兰氏阳性和革兰氏阴性细菌和六种真菌的生物学活性进行了探测.结果表明这些化合物没有抗菌活性,但是具有抗真菌活性.
    DOI:10.1016/j.Tetlet.2016.04.117

    海关参考信息

    专利信息


    专利号:US-7723082-B2
    优先权日:2002-06-21
    标题 :Polynucleotides and polypeptides coded by said polynucleotides involved in the synthesis of diketopiperazine derivatives
    发明人：GONDRY MURIEL; GENET ROGER; LAUTRU SYLVIE; PERNODET JEAN-LUC
    权利人:COMMISSARIAT ENERGIE ATOMIQUE; CENTRE NAT RECH SCIENT
    摘要:The invention concerns novel isolated natural or synthetic polynucleotides and polypeptides coded by said polynucleotides, involved in the synthesis of diketopiperazine derivatives, vectors comprising said polynucleotides, micro-organisms transformed with said polynucleotides, uses of said polynucleotides and said polypeptides, as well as methods for the synthesis of diketopiperazine derivatives, including cyclodipeptides and diketopiperazine derivatives 3- and 6-substituted by α,β-unsaturated amino acid side chains.

    专利号:US-2006051837-A1
    优先权日:2002-06-21
    标 题 :Polynucleotides and polypeptides coded by said polynucleotides involved in the synthesis of diketopiperazine derivatives

    专利号:US-2007048817-A1
    优先权日:2002-06-21
    标 题:Polynucleotides and polypeptides coded by said polynucleotides involved in the synthesis of diketopiperazine derivatives

    专利号:AU-2003255681-B2
    优先权日:2002-06-21
    标题:Polynucleotides and polypeptides coded by said polynucleotides involved in the synthesis of diketopiperazine derivatives

    专利号:AU-2003255681-A1
    优先权日:2002-06-21
    标题 :Polynucleotides and polypeptides coded by said polynucleotides involved in the synthesis of diketopiperazine derivatives

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    主要参考文献

    1. Stierle, A.C., Cardellina, J.H., and Strobel, G.A. Maculosin, a host-specific phytotoxin for spotted knapweed from Alternaria alternata. Proc. Natl. Acad. Sci. U.S.A. 85(21), 8008-8011 (1988). 2. Puopolo, G., Cimmino, A., Palmieri, M.C., et al. Lysobacter capsici AZ78 produces cyclo(L-Pro-L-Tyr), a 2,5-diketopiperazine with toxic activity against sporangia of Phytophthora infestans and Plasmopara viticola. J. Appl. Microbiol. 117(4), 1168-1180 (2014). 3. Wattana-Amorn, P., Charoenwongsa, W., Williams, C., et al. Antibacterial activity of cyclo(L-Pro-L-Tyr) and cyclo(D-Pro-L-Tyr) from Streptomyces sp. strain 22-4 against phytopathogenic bacteria. Nat. Prod. Res. 30(17), 1980-1983 (2016). 4. Cain, C.C., Lee, D., Waldo, R.H., III, et al. Synergistic antimicrobial activity of metabolites produced by a nonobligate bacterial predator. Antimicrob. Agents Chemother. 47(7), 2113-2117 (2003).

    合成参考文献


    参考文献:10.1021/np960095b
    摘要:Jayatilake GS, Thornton MP, Leonard AC, Grimwade JE, Baker BJ. Metabolites from an Antarctic sponge-associated bacterium, Pseudomonas aeruginosa. J Nat Prod. 1996 Mar;59(3):293–6. doi: 10.1021/np960095b.
    参考文献:10.1016/j.bmcl.2011.05.002
    摘要:Xu Z, Zhang Y, Fu H, Zhong H, Hong K, Zhu W. Antifungal quinazolinones from marine-derived Bacillus cereus and their preparation. Bioorganic & Medicinal Chemistry Letters. 2011 Jul;21(13):4005–7. doi: 10.1016/j.bmcl.2011.05.002.
    参考文献:10.1080/14786419.2015.1095747
    摘要:Wattana-Amorn P, Charoenwongsa W, Williams C, Crump MP, Apichaisataienchote B. Antibacterial activity of cyclo(L-Pro-L-Tyr) and cyclo(D-Pro-L-Tyr) from Streptomyces sp. strain 22-4 against phytopathogenic bacteria. Natural Product Research. 2015 Oct 15;30(17):1980–3. doi: 10.1080/14786419.2015.1095747.
    参考文献:10.1021/np50106a005
    摘要:Barrow CJ, Sun HH. Spiroquinazoline, a novel substance P inhibitor with a new carbon skeleton, isolated from Aspergillus flavipes. J Nat Prod. 1994 Apr;57(4):471–6. doi: 10.1021/np50106a005.
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