Fmoc-beta-Ala(SO3H)-OH

Code: FAA1915
CAS: 1005412-03-2 
Chemical Name: N-(9-Fluorenylmethyloxycarbonyl)-alpha-sulfo-beta-Alanine,
(SR)-3-(9-Fluorenylmethyloxycarbonylamino)-2-sulfo-propanoic acid
Formula: C₁₈H₁₇NO₇S
Mol. Weight: 391,4 g/mole

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H-beta-Ala(SO3H)-OH

Code: HAA1860
CAS: 15924-28-4 
Chemical Name: alpha-Sulfo-beta-Alanine, (SR)-3-Amino-2-sulfo-propanoic acid
Formula: C₃H₇NO₅S
Mol. Weight: 169,16 g/mole

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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 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.

Literature:
Anthony Romieu, Thomas Bruckdorfer, Guillaume Clavé, Virgile Grandclaude, Cédrik Massif and Pierre-Yves Renard; Org. Biomol. Chem. 2011; 9:5337.
Romieu, A. et al. Bioconjugate Chem. 2010, 51: 3304-3308.
Song Lin Niu, Gilles Ulrich, Raymond Ziessel, Agneta Kiss, Pierre-Yves Renard, Anthony Romieu; Org. Lett. 2009, 11(10): 2049-2052.
Romieu, A. et al. Bioconjugate Chem. 2008, 19: 279-289.
Wagner, D. et al. Tetrahedron Lett. 1968, 43: 4479-4480.