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Fmoc-beta-Ala(SO3H)-OH
Chemical name: (SR)-3-(9-Fluorenylmethyloxycarbonylamino)-2-sulfo-propanoic acid // Synonyms: N-(9-Fluorenylmethyloxycarbonyl)-alpha-sulfo-beta-Alanine
- Product code:FAA1915
- CAS No.:1005412-03-2
- Storage temperature:2-8°C
- Formula:C18H17NO7S
- Molecular weight:391.4 g/mol
from €200.00
description
alpha-Sulfo-beta-Alanine has been used to couple to hydrophobic labels like Cyanine and Rhodamine dyes and other hydrophobic residues to increase their solubility in water. As di-or tripeptide a further increase of hydrophilicity can be achieved. Fmoc-beta-Ala(SO3H)-OH (FAA1915) can be coupled in SPPS by standard phosphonium or uronium based coupling reagents. In high throughput technologies for DNA sequencing and genomics charge-modified dye-labeled dideoxynucleoside-5’ -triphosphates were synthesized for ‘direct-load’ applications in DNA sequencing.
references
New insights into the water-solubilization of thiol-sensitive fluorogenic probes based on long-wavelength 7-hydroxycoumarin scaffolds; B. Roubinet, P.-Y. Renard and A. Romieu; Dyes and Pigments 2014; 110: 270-284. doi:http://dx.doi.org/10.1016/j.dyepig.2014.02.004.
N-Fmoc-alpha-sulfo-beta-alanine: a versatile building block for the water solubilisation of chromophores and fluorophores by solid-phase strategy; A. Romieu, T. Bruckdorfer, G. Clave, V. Grandclaude, C. Massif and P.-Y. Renard; Organic & Biomolecular Chemistry 2011; 9: 5337-5342. doi:10.1039/c1ob05730h.
Water solubilization of xanthene dyes by post-synthetic sulfonation in organic media; A. Romieu, D. Tavernier-Lohr, S. Pellet-Rostaing, M. Lemaire and P.-Y. Renard; Tetrahedron Letters 2010; 51: 3304-3308. doi:http://dx.doi.org/10.1016/j.tetlet.2010.04.080.
Water-Soluble BODIPY Derivatives; S. L. Niu, G. Ulrich, R. Ziessel, A. Kiss, P.-Y. Renard and A. Romieu; Org Lett 2009; 11: 2049-2052. doi:10.1021/ol900302n.
Postsynthetic Derivatization of Fluorophores with a-Sulfo-b-alanine Dipeptide Linker. Application to the Preparation of Water-Soluble Cyanine and Rhodamine Dyes; A. Romieu, D. Brossard, M. Hamon, H. Outaabout, C. Portal and P.-Y. Renard; Bioconjug Chem 2007; 19: 279-289. doi:10.1021/bc7003268.
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