CAS: 13139-14-5; Boc-Trp-Oh

该化合物是L-tryptophan 受保护的衍生物,在α-氨基位置上有一个三丁基碳基(Boc)组,这种改变增强了稳定性,防止了在peptide合成过程中出现不必要的侧面反应,使其成为固相和溶解阶段的peptide化学中有价值的中间体.Boc 组很容易在温和的酸条件下被切除,允许有选择地去保护而不影响其他功能组.该组保留了treptophan的单端链条,使其能够融入需要芳香或缺水残留物的peptide,其高纯度和一贯性能使其适合研究和制药应用,特别是在复杂的peptide和生物活性分子的合成中.

结构式图片

相似化合物

5241-64-5 112525-72-1 143824-78-6

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

    1-(1H-Indol-3-yl)-N,N,N-Trimethylmethanaminium Methyl Sulfate置于氨,Lithium,Lithium Hexamethyldisilazane,叔丁醇体系中,用 四氢呋喃 用作溶剂,化学反应 2.5H,反应生成N-叔丁氧羰基-L-色氨酸
    参考文献:通过手性甘氨酸烯醇盐等效物与季胺的烷基化合成色氨酸
    标题:通过手性甘氨酸烯醇盐等效物与季胺的烷基化合成色氨酸
    摘要:发现季胺是非对映选择性烷基化的3-甲基吲哚片段的合适来源.对于手性william'S吗啉代烯醇烯酸酯的烷基化,可获得最佳收率和立体选择性.基于该转化,开发了具有非常好总收率的对映体纯的,吲哚环取代的色氨酸衍生物的合成的通用方法.
    Doi:10.1016/j.Tetlet.2015.09.017

    海关参考信息

    专利信息


    专利号:US-6815214-B2
    优先权日:2000-12-29
    标 题 :Pharmaceutical uses and synthesis of diketopiperazines
    发明人:BOYCE JIM P; HOWBERT J JEFFRY; TABONE JOHN C
    权利人:CELLTECH R & D INC
    摘要:The synthesis of novel diketopiperazines, their use in inhibiting cellular events such as those involving NFK-α, NFK-β and in the treatment of inflammation events, a combinatorial library of diverse diketopiperazines and process for their synthesis as a library and as individual compounds. In particular novel diketopiperazines are disclosed including their synthesis and use in cellular events such as activation of the transcription factor, nuclear factor, TNF-α, TNF-β and also apoptosis.

    专利号:US-2018265547-A1
    优先权日:2014-07-18
    标 题 :Z-selective olefin metathesis of peptides
    发明人:MANGOLD SHANE L; GRUBBS ROBERT H
    权利人:CALIFORNIA INST OF TECHN
    摘要:The invention relates generally to the synthesis of modified amino acids and modified peptides in the presence of cyclometalated catalysts. The invention has utility in the fields of catalysis, organic synthesis, polymer chemistry, and industrial and fine chemicals chemistry.

    专利号:US-2007179279-A1
    优先权日:2005-12-30
    标题:Methods for the synthesis of arginine-containing peptides
    发明人:CHEN LIN; ROBERTS CHRISTOPHER R
    权利人:CHEN LIN; ROBERTS CHRISTOPHER R
    摘要:Methods for the synthesis of arginine-containing peptides are provided. The methods include a step that minimizes contact of side chain protected arginine with base prior to the coupling step.

    专利号:US-7122628-B2
    优先权日:2000-12-22
    标 题:Process for the synthesis of a peptide having a Trp residue
    发明人:JACKSON STEVEN ALLEN
    权利人:IPSEN MFG IRELAND LTD
    摘要:A process for the solid phase synthesis of a peptide having at least one thyptophan residue, wherein said method comprises temporarily protecting the indole ring of said tryptophan residue with a side chain protecting group which is labile to a base wherein said protecting group is removed during cleavage of said peptide from the solid support.

    专利号:US-12378196-B2
    优先权日:2018-12-11
    标 题 :Synthesis of (S)-6-hydroxytryptophan and derivatives thereof
    发明人:SIMON WERNER; WERNER-SIMON SUSANNE; MüLLER CHRISTOPH
    权利人:HEIDELBERG PHARMA RES GMBH
    摘要:The present invention relates to novel methods and compounds for synthesizing amanitin derivatives. The invention in particular relates to methods for synthesizing (S)-6-hydroxy-tryptophan derivatives which can be used as building blocks for synthesizing amanitin derivatives or amatoxin drug conjugates. The invention further relates to intermediate compounds of said synthesis pathways for use in amanitin derivative and amatoxin drug conjugate synthesis, and to the use of particular catalysts suited for mediating said synthesis pathways.

    专利号:US-3790555-A
    优先权日:1972-01-20
    标 题:Octapeptide derivative of gonadotropinreleasing hormone
    发明人:FLOURET G; COLE J
    权利人:ABBOTT LAB
    摘要:THE SYNTHESIS OF THE OCTAPEPTIDE TRP-SER-TYR-GLY-LEUARG-PRO-GLY-AMIDE CARRYING EASILY REMOVABLE PROTECTIVE GROUPS ON THE SER, TYR, ARG AND TRP MOIETIES IS DESCRIBED. THE NEW SYNTHESIS USES AS THE STARTING MATERIAL TWO TETRAPEPTIDE FRAGMENTS CARRYING EASILY REMOVABLE PROTECTIVE GROUPS. ONE OF THESE FRAGMENTS, TRP-SER-TYR-GLY-OH WITH SUITABLE PROTECTIVE GROUPS, ALSO IS A PART OF THE PRESENT INVENTION. AFTER COUPLING OF THE TWO FRAGMENTS, THE PROTECTIVE GROUP ON THE AMINO-N OF THE TRYPTOPHANE MOIETY IS REMOVED TO OBTAIN AN OCTAPEPTIDE CARRYING EASILY REMOVABLE PROTECTIVE GROUPS WHICH CAN BE RETAINED VHILE BULIDING UP THE MOLECULE TO THE DECAPEPTIDE CHAIN WHICH IS THE GONADOTROPIN-RELEASING HORMONE, AFTER REMOVAL OF THESE PROTECTIVE GROUPS.
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    📌 第三方产品分析报告

    ✅ COA系统入驻 | 共享模式

    主要参考文献

    参考标题:5-Norbornene-2,3-Dicarboximido Carbonochloridate. A New Stable Reagent For The Introduction Of Amino-Protecting Groups
    作者:Peter Henklein,Hans-Ulrich Heyne,Wolf-Rainer Halatsch,Hartmut Niedrich
    摘要:The Synthesis Of Activated Carbonates, Based On A New Carbonochloridate Derived From N-Hydroxy-5-Norbornene-2,3-Dicarboximide, Is Reported. These Activated Carbonic Esters Are Excellent Reagents For The Introduction Of All Currently Used Urethane Protecting Groups.

    合成参考文献


    摘要:Wessjohann, L. A.; Kaluđerović, G. N.; Neves Filho, R. A. W.; Morejon, M. C.; Lemanski, G.; Ziegler, T., Science of Synthesis: Multicomponent Reactions, (2013) 1, 495.
    摘要:Kroon, E.; Zarganes Tzitzikas, T.; Neochoritis, C. G.; Dömling, A., Science of Synthesis: Applications of Domino Transformations in Organic Synthesis, (2015) 2, 428.
    摘要:Kleemann A., Kutscher B., Reichert D., Bossart M., Pharmaceutical Substances, Thieme [Online], Stuttgart, (2025).
    摘要:Leclerc, E., Science of Synthesis: Knowledge Updates, (2024) 3, 243.
    参考文献:10.1063/1.2216696
    摘要:Mitchell SA. Origin of second harmonic generation optical activity of a tryptophan derivative at the air/water interface. J Chem Phys. 2006 Jul 28;125(4):44716. doi: 10.1063/1.2216696.
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