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Fmoc-N-propargyl-MPBA
Chemical name: 4-(4-(((9-Fluorenylmethyloxycarbonyl)(propargyl)amino)methyl)-3-methoxyphenoxy)butanoic acid // Synonyms: 4-(4-(((((9H-fluoren-9-yl)methoxy)carbonyl)(prop-2-yn-1-yl)amino)methyl)-3-methoxyphenoxy)butanoic acid, 4-(3-methoxy-4-[(Fmoc)(propargyl)aminomethyl]-phenoxy-butanoic acid
- Product code:RL-3780
- CAS No.:1009362-00-8
- Formula:C30H29NO6
- Molecular weight:499.20 g/mol
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description
A propargyl-substituted MPBA linker derived from 4-hydroxy-3-methoxybenzaldehyde, which can be elongated using standard Fmoc-based solid phase chemistry and linked to supports by standard coupling procedures. The benzylic bond can be cleaved by addition of 90% TFA with appropriate scavengers.
This linker is reported to enable access to triazole-containing cyclic pseudopeptides.
references
Synthesis of a biologically active triazole-containing analogue of cystatin A through successive peptidomimetic alkyne-azide ligations; I. E. Valverde, F. Lecaille, G. Lalmanach, V. Aucagne, A. F. Delmas; Angew. Chem. Int. Ed. Engl. 2012; 51(3): 718-722. https://doi.org/10.1002/anie.201107222.
Biomimetic Screening of Class-B G Protein-Coupled Receptors; C. Devigny, F. Perez-Balderas, B. Hoogeland, S. Cuboni, R. Wachtel, C. P. Mauch, K. J. Webb, J. M. Deussing, F. Hausch; J. Am. Chem. Soc. 2011; 133(23): 8927-8933. https://doi.org/10.1021/ja200160s.
Backbone Amide Linker Strategy for the Synthesis of 1,4-Triazole-Containing Cyclic Tetra- and Pentapeptides; J. Springer, K. R. de Cuba, S.
Calvet-Vitale, J. A. J. Geenevasen, P. H. H. Hermkens, H. Hiemstra, J. H. van Maarseveen; Eur. J. Chem. 2008; 15: 2592-2600. https://doi.org/10.1002/ejoc.200800143.
An alternative method for the preparation of resin-bound secondary amines; R. E. Austin, C. A. Waldraff, F. Al-Obeidi; Tetrahedron Lett. 2002; 43(19): 3555-3556. https://doi.org/10.1016/S0040-4039(02)00569-5.
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