CAS: 16063-80-2; 4,4,4,4',4',4'-Hexafluoro-Dl-Valine

该化合物是氨基酸valine的氟化衍生物,其特点是在结构中替换六氟原子,这种改变增强了其脂性性和代谢稳定性,使其在peptide合成和药用化学中具有价值.氟原子的存在提高了抗酶降解的能力,提高了含有这种非天然氨基酸的的生用利用率.其种族(DL)形式允许多种用途地应用于研究和药物开发.六氟-DL-valine在设计生物活性类氟特别有用,因为在那里,人们希望加强薄膜的渗透性并延长活性稳定性.它作为先进的制药和生物化学研究的关键基石.

结构式图片

相似化合物

1214705-90-4 1098184-03-2 107496-46-8

欧盟法规

ECHA物质ECHA物质C&L通报REACH预注册

上下游产品

CAS号107496-45-7 DL-hexafluorova... | CAS号78185-92-9 2-氨基-4,4,4-三氟-3... | CAS号107496-44-6 benzyl β,β-bis(... | CAS号1513-60-6 4,4,4-三氟-3-三氟甲基丁酸乙酯 | CAS号78164-91-7 DL-hexafluorova... | CAS号759-25-1 Hexafluorisopro... | CAS号2711-61-7 2-Amino-2-hexaf... | CAS号1763-28-6 4,4,4-三氟-3-(三氟甲基)巴豆酸

合成工艺路线路线简述

  • 合成目标产物 Hexafluoro-Dl-Valine 主要起始原料 4,4,4,4',4',4'-Hexafluorovaline,Ethylester
  • (文献来源)合成步骤主要原料 4,4,4,4',4',4'-Hexafluorovaline,Ethylester
4,4,4-三氟-3-三氟甲基丁酸乙酯置于盐酸,氨体系中,用 乙醚 用作溶剂,化学反应 10.67H,反应生成4,4,4,4',4',4'-六氟-Dl-缬氨酸
参考文献:含氟肽的合成.含有六氟缬氨酸的血管紧张素ii的类似物.
标题:含氟肽的合成.含有六氟缬氨酸的血管紧张素ii的类似物.
摘要:已经制备了γ,γ,γ,γ,六氟缬氨酸及其衍生物,并通过片段缩合和固相肽合成将其掺入血管紧张素ii中.六氟缬氨酸衍生物显示出对各种酶消化的一般抵抗力,并且在羧基活化后具有广泛消旋的趋势.当在大鼠子宫上测定血管紧张素ii类似物时,[hfv5] Aii具有133%的活性,[d-Hfv5] Aii没有活性,[ac-Asn1,Dl-Hfv8] Aii在体外是一种有效的血管紧张素ii抑制剂.体内.
Doi:10.1021/jm00141A005

海关参考信息

专利信息


专利号:US-9206222-B2
优先权日:2009-06-29
标题:Solid phase peptide synthesis of peptide alcohols
发明人:CAUSSIL-AMBLARD MURIEL; MARTINEZ JEAN; TAILHADES JULIEN
权利人:CAUSSIL-AMBLARD MURIEL; MARTINEZ JEAN; TAILHADES JULIEN; CENTRE NAT RECH SCIENT
摘要:The present invention relates to the synthesis of depsipeptides on solid phase support. Said depsipeptides are then implicated in a solution phase O—N acyl shift enabling to obtain the corresponding peptide alcohols.

专利号:US-7371867-B2
优先权日:2001-02-27
标题 :Non-racemic trifluoroleucine, and methods of making and using
发明人:FICHERA ALFIO; BILGICER ZIHNI; KUMAR KRISHNA; XING XUECHAO
权利人:TUFTS COLLEGE
摘要:One aspect of the invention relates to hexafluoroleucine and congeners thereof, and methods of making the compounds. Another aspect of the invention relates to the synthesis of protein cores comprising hexafluoroleucine and congeners thereof. Certain peptides comprising hexafluoroleucine and congeners thereof have been characterized using comparative biophysical studies. In general, the fluorinated peptides show higher thermal stability and enhanced resistance to chemical denaturation. Further, mixed hydrocarbon-fluorocarbon cores self-sort into homogeneous bundles, suggesting new avenues for the design and manipulation of protein-protein interfaces.

专利号:US-8546533-B2
优先权日:2008-08-29
标 题:Pipecolic linker and its use for chemistry on solid support
发明人:MARTINEZ JEAN; ZAJDEL PAWEL; PAWLOWSKI MACIEJ; SUBRA GILLES
权利人:MARTINEZ JEAN; ZAJDEL PAWEL; PAWLOWSKI MACIEJ; SUBRA GILLES; CENTRE NAT RECH SCIENT; UNIV MONTPELLIER 1; UNIV JAGELLONE; UNIV MONTPELLIER II
摘要:The present invention relates to a pipecolic linker and its use as a solid-phase linker in organic synthesis. Said pipecolic solid-phase linker may be used for coupling functional groups chosen between primary amines, secondary amines, aromatic amines, alcohols, phenols and thiols. In particular, said pipecolic solid-phase linker may be used for peptide or pseudopeptide synthesis, such as the reverse N to C peptide synthesis or the retro-inverso peptide synthesis, or for the synthesis of small organic molecules.

专利号:WO-2011000848-A1
优先权日:2009-06-29
标题 :Solid phase peptide synthesis of peptide alcohols

专利号:US-11759496-B2
优先权日:2016-05-10
标题:Compounds and pharmaceutical use thereof in the treatment of cancer
发明人:SUSIN SANTOS A; KAROYAN PHILIPPE; MERLE-BERAL HÉLÈNE
权利人:KAROYAN PHILIPPE
摘要:The present invention relates to a compound or a pharmaceutical salt thereof comprising a hexapeptide sequence of formula (I), its method of synthesis and its use in anticancer therapy. The invention also relates to a pharmaceutical composition for use in the treatment of cancer comprising at least one soluble peptide according to the invention or at least one acid nucleic according to the invention or at least one expression vector according to the invention, or at least one host cell according to the invention and a pharmaceutically acceptable carrier.

专利号:US-2012108748-A1
优先权日:2009-06-29
标 题:Solid phase peptide synthesis of peptide alcohols
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主要参考文献

[参考文献]: W H Vine, Et Al. Synthesis Of Fluorine-Containing Peptides. Analogues Of Angiotensin Ii Containing Hexafluorovaline. J Med Chem. 1981 Sep;24(9):1043-7.

合成参考文献


参考文献:10.1016/j.antiviral.2011.06.006
摘要:Campagnola G, Gong P, Peersen OB. High-throughput screening identification of poliovirus RNA-dependent RNA polymerase inhibitors. Antiviral Research. 2011 Sep;91(3):241–51. doi: 10.1016/j.antiviral.2011.06.006.
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