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HS-(CH2)m-NHCOO-Coumarin-7-O(CH2)9-CH3 (PC 002)


Yet another great example of unique coumarin-4-ylmethyl photocleavablethiol for UV-patterned SAMs applications that is usefulalternative to productCat no. PC 001-m10-0.05orPC 001-m10-0.1 The photo-cleavable protecting groups are called "phototriggers" or "caging groups". Coumarin-4-ylmethyls are phototriggers with higher efficiencies than others such 2-nitro-benzyls, enabling the incident light intensity for the uncaging reaction to be lowered. It leads to minimization of protected functionality damage with maintaining higher spatial and temporal resolution. The coumarin-type cages have been successfully applied to protect phosphates [1, 2], amines [3], carboxylates [4], alcohols and phenols [5]. The N-(11-sulfanylundecan-1-yl)-7-decyloxy-2-oxo-2H-chromen-4-ylmethyl carbamate (Cat no: PC 002-m10-0.05, PC 002-m10-0.1) after uncaging reaction (350 nm irradiation) provides amine group at the surface of SAMs available for interaction or further functionalization. These coumarin-type phototriggers were also applied for modification of SAMs surfaces properties [6-8]. Using irradiation with light to alter the cell adhesiveness of a substrate surface allows for patterning of cell cultures in various shapes and sizes without compromising the bioinert character of the non-irradiated regions.

[1] Furuta, T.; Torigai, H.; Sugimoto, M.; Iwamura, M. J. Org. Chem. 1995, 60, 3953-3956.
[2] Schade, B.; Hagen V.; Schmidt, R.; Herbrich, R.; Krause, E.; Eckardt, T.; Bendig, J. J. Org. Chem. 1999, 64, 9109-9117.
[3] Montgomery, H.J.; Perdicakis, B.; Fishlock, D.;Lajoie, G. A.; Jervis, E.; Guillemette, J. G. Bioorg. Med. Chem. 2002, 10, 1919-1927.
[4] Ito, K.; Sawanobori, J. Synth. Commun. 1982, 12, 665-671.
[5] Suzuki, A. Z.; Watanabe, T.; Kawamoto, M.; Nishiyama, K.; Yamashita, H.; Ishii, M.; Iwamura, M.; Furuta, T. Org. Lett. 2003, 5, 4867-4870.
[6] Robertus, J.; Browne, W. R.; Feringa, B. L. Chem. Soc. Rev., 2010, 39, 354–378.
[7] Cheng, N; Cao, X. J. Colloid Interface Sci. 2010, 348, 71-79.
[8] Mancini, R. J.; Li, R. C.; Tolstyka, Z. P.; Maynard, H. D. Org. Biomol. Chem., 2009, 7, 4954–4959.

Standard Products

name catalog no. m n weight price
HS-C11-N(H)COO-coumarin-7-O-C9-Me PC 002-m11-0.05 11 50 mg Log in to see the prices
HS-C11-N(H)COO-coumarin-7-O-C9-Me PC 002-m11-0.1 11 100 mg

Custom synthesis variants

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