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

Description

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

Note, if none of the listed structures fit your specific requirements, please submit your own structure formula within our custom synthesis contact form by clicking button below.

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