CAS: 73724-46-6; Fmoc-Ser-Obzl

该化合物是一种受保护的精液衍生物,广泛用于peptide合成.Fmoc (9-氟甲基苯氧碳基)组为α-氨组提供了正方位保护,在温和基本条件下有选择地取消保护,而苯基(Obzl)酯则保障了碳oxyl组不被过早激活.该化合物在固相合成中特别宝贵,其稳定性和与标准的氟化物议定书的兼容性确保高联效.其晶体形式提高了处理精度,而苯基酯可以通过氢解析法进行脱硫化,从而提供灵活性.Fmoc-Ser-Obzl(Obzl)是建造含有醋残留物的复杂peptid的可靠建筑块.

结构式图片

相似化合物

116861-26-8 141527-78-8 59524-02-6

上下游产品

L-serine benzyl ester N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide L-serine benzyl ester hydr°Chloride (fluorenylmethoxy)carbonyl chloridebenzyl-N-(fluorenylmethyloxycarbonyl)-O-(2,3,4,6-tetra-O-benzoyl β-D-glucopyranosyl) L-serinate benzyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-serinate -L-serine benzyl esterFm°C-O-3,4,6-tri-O-benzyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-β-D-mannopyranosyl-L-serine benzyl ester -L-serine benzyl esterFm°C-O-3,4,6-tri-O-benzyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranosyl-L-serine benzyl ester

合成工艺路线路线简述

    📜9-芴甲基-N-琥珀酰亚胺基碳酸酯置于sodium Carbonate,Caesium Carbonate体系中,用 1,4-二氧六环,甲醇,水 作为反应溶剂,化学反应 0.25H,反应生成 Fmoc-O-苄基-L-丝氨酸
    参考文献:Influence Of Steric Parameters On The Synthesis Of Tetramates From α-Amino-β-Alkoxy-Esters And Ph3Pcco
    标题:Influence Of Steric Parameters On The Synthesis Of Tetramates From α-Amino-β-Alkoxy-Esters And Ph3Pcco
    摘要:Alpha-Aminoesters React With Ph3Pcco In A Domino Addition-Wittig Cyclization Sequence Affording Enantiomerically Pure Tetramates. In The Case Of Beta-Oxo Functionalized Alpha-Aminoesters,E.G.,Esters Of Serine,Threonine Or Beta-Hydroxyornithine The Yields Of This Reaction Depend Heavily On The Bulkiness Of The Beta-Or Group And On The Configuration Of Beta-Carbon Atom C-3. Smaller Residues And 2R/3R-Configured Aminoesters Give Better Yields. The Alkoxycarbonyl Group Of The Ester Moiety And The Residue On The N-Atom Are Less Important. These Findings Can Be Accounted For By Assuming An Early Puckered Transition State For The Intramolecular Ring-Closing Wittig Reaction. The Addition Of Sub-Stoichiometric Amounts Of Benzoic Acid Or N-Hydroxysuccinimide (For Acid-Sensitive Compounds) Is Advantageous In Some Cases As It Accelerates The Formation Of The Intermediate Amide Ylides. (C) 2011 Elsevier Ltd. All Rights Reserved.
    DOI:10.1016/j.Tet.2011.10.099

    海关参考信息

    专利信息


    专利号:US-7160856-B2
    优先权日:1997-04-16
    标 题 :α-O-linked glycoconjugates, methods of preparation and uses thereof
    发明人:DANISHEFSKY SAMUEL J; SAMES DALIBOR; HINTERMANN SAMUEL; CHEN XIAO TAO; SCHWARZ JACOB B; GLUNZ PETER; RAGUPATHI GOVINDASWAMI; LIVINGSTON PHILIP O; KUDUK SCOTT; WILLIAMS LAWRENCE
    权利人:SLOAN KETTERING INST CANCER
    摘要:The present invention provides novel alpha-O-linked glycoconjugates such as alpha-O-linked glycopeptides, as well convergent methods for synthesis thereof. The general preparative approach is exemplified by the synthesis of the mucin motif commonly found on epithelial tumor cell surfaces. The present invention further provides compositions and methods of treating cancer using the alpha-O-linked glycoconjugates.

    专利号:US-7550146-B2
    优先权日:1997-04-16
    标 题 :Glycopeptide conjugates and uses thereof
    发明人:DANISHEFSKY SAMUEL J; SAMES DALIBOR; HINTERMANN SAMUEL; GLUNZ PETER; RAGUPATHI GOVINDASWAMI; LIVINGSTON PHILIP O; LLOYD KENNETH O; KUDRYASHOV VALERY
    权利人:SLOAN KETTERING INST CANCER
    摘要:The present invention provides novel glycoconjugates such as glycopeptides, as well as convergent methods for the synthesis thereof. An exemplary preparative approach is exemplified by the synthesis of the mucin motif commonly found on epithelial tumor cell surfaces. The present invention further provides compositions and methods of treating cancer using the glycoconjugates of the invention.

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    品牌试剂参考报价(招募中)

    📌 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:Chemical Synthesis Of A Heparan Sulfate Glycopeptide: Syndecan-1
    作者:Bo Yang,Keisuke Yoshida,Zhaojun Yin,Hang Dai,Herbert Kavunja,Mohammad H. El-Dakdouki,Suttipun Sungsuwan,Steven B. Dulaney,Xuefei Huang |发布日期:2012.10.1
    摘要:Assembled. The Protective Groups Utilized, As Well As The Sequences For Formation Of The Glycosyl Linkages And Protecting Group Removal Are Critical To The Success Of The Synthesis. This First Preparation Of A Heparan Sulfate Glycopeptide Lays The Foundation For Accessing Other Members Of This Class Of Molecules.

    合成参考文献


    参考文献:10.1055/s-0036-1588691
    摘要:Liu S, Liu J, Li X, Yuan L, Wang Q, Liang L, Huang G. Solid-Phase Synthesis of a Special Phosphorylated Peptide as a Biomarker for LC–MS/MS Detection for OPNA Exposure. Synlett. 2017 Mar 01;28(08):986–8. doi: 10.1055/s-0036-1588691.
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