S-Fluorenylmethyl protection of the cysteine side chain upon Nα-Fmoc deprotection

作者: Johannes W Wehner , Thisbe K Lindhorst

DOI: 10.3762/BJOC.8.242

关键词:

摘要: Deprotection of an N(α)-Fmoc-protected glycocysteine derivative 7 with excess morpholine unexpectedly led to the fluorenylmethyl-protected thioether 8 in high yield. The suggested mechanism for this reaction comprises addition cysteine thiolate on exocyclic double bond dibenzofulvene, which is formed during Fmoc deprotection. influence base concentration transprotection was studied.

参考文章(19)
Louis A. Carpino, Grace Y. Han, 9-Fluorenylmethoxycarbonyl function, a new base-sensitive amino-protecting group Journal of the American Chemical Society. ,vol. 92, pp. 5748- 5749 ,(1970) , 10.1021/JA00722A043
Alexander Schierholt, Mirja Hartmann, Kirsten Schwekendiek, Thisbe K. Lindhorst, Cysteine-Based Mannoside Glycoclusters: Synthetic Routes and Antiadhesive Properties European Journal of Organic Chemistry. ,vol. 2010, pp. 3120- 3128 ,(2010) , 10.1002/EJOC.201000185
Alexander Schierholt, Harun A. Shaikh, Jörn Schmidt-Lassen, Thisbe K. Lindhorst, Utilizing Staudinger Ligation for the Synthesis of Glycoamino Acid Building Blocks and Other Glycomimetics European Journal of Organic Chemistry. ,vol. 2009, pp. 3783- 3789 ,(2009) , 10.1002/EJOC.200900437
Thisbe Lindhorst, Johannes Wehner, Glycocluster Synthesis by NativeChemical Ligation Synthesis. ,vol. 2010, pp. 3070- 3082 ,(2010) , 10.1055/S-0030-1258157
Christian P. R. Hackenberger, Dirk Schwarzer, Chemoselektive Ligations‐ und Modifikationsstrategien für Peptide und Proteine Angewandte Chemie. ,vol. 120, pp. 10182- 10228 ,(2008) , 10.1002/ANGE.200801313
David P. Gamblin, Eoin M. Scanlan, Benjamin G. Davis, Glycoprotein synthesis: an update. Chemical Reviews. ,vol. 109, pp. 131- 163 ,(2009) , 10.1021/CR078291I
Géza Zemplén, Eugen Pacsu, Über die Verseifung acetylierter Zucker und verwandter Substanzen Berichte der deutschen chemischen Gesellschaft (A and B Series). ,vol. 62, pp. 1613- 1614 ,(1929) , 10.1002/CBER.19290620640
Mirja Hartmann, Thisbe K. Lindhorst, The Bacterial Lectin FimH, a Target for Drug Discovery – Carbohydrate Inhibitors of Type 1 Fimbriae‐Mediated Bacterial Adhesion European Journal of Organic Chemistry. ,vol. 2011, pp. 3583- 3609 ,(2011) , 10.1002/EJOC.201100407
Harun A. Shaikh, Frank D. Sönnichsen, Thisbe K. Lindhorst, Synthesis of glycocluster peptides Carbohydrate Research. ,vol. 343, pp. 1665- 1674 ,(2008) , 10.1016/J.CARRES.2008.04.015
Hilbert M. Branderhorst, Rob M.J. Liskamp, Roland J. Pieters, Solid-phase carbohydrate synthesis via on-bead protecting group chemistry Tetrahedron. ,vol. 63, pp. 4290- 4296 ,(2007) , 10.1016/J.TET.2007.03.051