CAS: 129046-87-3; (S)-4-((9H-Fluoren-9-yl)Methoxy)-3-((Tert-Butoxycarbonyl)Amino)-4-Oxobutanoic Acid

该化合物是受保护的,在peptide合成中广泛使用的分离酸衍生物, 乙型丁氧碳基(Boc)组保护α-氨基组, 而氟乙基甲基(OFm)酯保护碳酸酯功能, 确保在固相或溶相peptide组装期间有选择性地取消保护. 这种化合物对于其正方位保护战略特别有用, 允许在温酸(Boc)或基本(OFm)条件下有控制的连续保护. 它的高度纯度和稳定性使它适合复杂的pept合成, 尽量减少侧反应. 生物化学和生物化学研究通常使用这种化合物, 以精确的再生化学控制来制造peptid.

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129460-09-9 134098-70-7 117014-32-1

上下游产品

9-Fluorenylmethanol N-tert-butyloxycarbonylaspartic acid anhydride tert-butyl dicarbonatedi-tert-butyl dicarbonate B°C-Asp-OH2-(tert-butoxycarbonyl)-N4-[2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1-4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl]-L-asparagine fluorenylmethyl esterN2-(tert-butoxycarbonyl)-N4-[2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl-(1-4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl]-L-asparagine fluorenylmethyl ester

合成工艺路线路线简述

    📜二碳酸二叔丁酯置于n,N-二甲氨基-2-氯丙烷盐酸盐,Sodium Carbonate,N,N-二异丙基乙胺体系中,用 四氢呋喃,水 用作溶剂,化学反应 52.0H,反应生成N-叔丁氧羰基-L-天冬氨酸 1-(9H-芴-9-基甲基)酯
    参考文献:An Unexpected Product From Attempted Reductive Etherification Of A Silyl Alcohol With An Aldehyde
    标题:An Unexpected Product From Attempted Reductive Etherification Of A Silyl Alcohol With An Aldehyde
    摘要:Reductive Etherification,Using Bibr3/et3Sih,Between Two Modified Amino Acids,One With A Silyl Alcohol Side Chain And One With An Aldehyde Side Chain,Gave,Not The Desired Bis-Amino Acid,But A Tetrahydrooxazine,In Good Yield. (C) 2007 Elsevier Ltd. All Rights Reserved.
    Doi:10.1016/j.Tet.2007.03.163

    海关参考信息

    专利信息


    专利号:US-6008058-A
    优先权日:1993-06-18
    标 题:Cyclic peptide mixtures via side chain or backbone attachment and solid phase synthesis
    发明人:SPATOLA ARNO F; DARLAK KRZYSZTOF; WEN JAMES JUN; ROMANOVSKIS PETERIS
    权利人:UNIV LOUISVILLE RES FOUND
    摘要:A method of preparing cyclic peptide mixtures via side chain or backbone and solid phase synthesis. The cyclic peptide mixtures form libraries that are useful for screening purposes featuring the attachment of an amino acid to a solid support through its side chain or backbone in order to mimic solution cyclization procedures with linear peptides. In the preferred embodiment, Boc chemistry is used for peptide synthesis, wherein the initial attachment of a trifunctional amino acid is by the aspartyl side chain (with OFm for alpha-carboxyl protection). Cyclization is performed using uronium reagents with racemization suppressant, and a strong acid (HF) is used for deprotection and cleavage. The strategy has been used for the preparation of a series of cyclic peptide mixtures. The procedure is expandable to include at least twenty different amino acids at each position (except the resin linked position where most attachments are by Asp, Lys, Glu, or Orn). The cyclic peptide mixtures vary in ring size from about four to about twelve residues.

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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:Synthesis Of A Glycosylated Peptide Thioester By The Boc Strategy And Its Application To Segment Condensation
    作者:Eiichiro Haginoya,Hironobu Hojo,Yuko Nakahara,Yoshiaki Nakahara,Kazuki Nabeshima,Bryan P. Toole,Yasushi Watanabe |发布日期:2006.6.23
    摘要:The Synthesis Of A Chitobiosylated Peptide Thioester By The T-Butoxycarbonyl (Boc) Strategy Is Demonstrated. Boc-Asn Carrying Benzyl-Protected Chitobiose Was Introduced During Application Of The Boc Mode Solid-Phase Method. Hf Treatment Of The Resulting Protected Peptide Resin Gave The Desired Chitobiosylated Peptide Thioester. This Thioester Was Used To Prepare The Peptide Sequence Derived From Extracellular Matrix Metalloproteinase Inducers (Emmprin) (34-94), (34-118) And (22-118) By The Thioester Segment Condensation Method. The Conformation Of These Glycopeptides Is Characterized By Circular Dichroism (Cd) Spectral Measurement.

    合成参考文献


    参考文献:10.1111/j.1399-3011.1990.tb00940.x
    摘要:AL‐OBEIDI F, SANDERSON DG, HRUBY VJ. Synthesis of β and γ‐fluorenylmethyl esters of respectively Nα‐Boc‐L‐aspartic acid and Nα‐Boc‐L‐glutamic acid. International Journal of Peptide and Protein Research. 1990 Mar;35(3):215–8. doi: 10.1111/j.1399-3011.1990.tb00940.x.
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