|
Peptide Nucleic Acid Monomers: A Convenient and Efficient Synthetic Approach to Fmoc/Boc Monomers
Elisse C.
Browne
A
,
Steven J.
Langford
B
and
Belinda M.
Abbott
A
C
A
La Trobe Institute of Molecular Science and Department of Chemistry, La Trobe University, Bundoora, Vic. 3086, Australia.
B
School of Chemistry, Monash University, Clayton, Vic. 3800, Australia.
C
Corresponding author. Email: b.abbott@latrobe.edu.au
Australian Journal of Chemistry
65(5)
539-544 http://dx.doi.org/10.1071/CH11471
Submitted: 12 December 2011 Accepted: 10 February 2012 Published:
14
May
2012
|  |
|
|
Abstract
A convenient and cost-effective method for the synthesis of Fmoc/Boc-protected peptide nucleic acid monomers is described. The Fmoc/Boc strategy was developed in order to eliminate the solubility issues during peptide nucleic acid solid-phase synthesis, in particular that of the cytosine monomer, that occurred when using the commercialized Bhoc chemistry approach. 
|
References
[1]
P. E. Nielsen, Science 1991, 254, 1497.
| CrossRef | CAS | 
[2]
K. L. Dueholm, M. Egholm, C. Behrens, L. Christensen, H. F. Hansen, T. Vulpius, K. H. Petersen, R. H. Berg, P. E. Nielsen, O. Buchardt, J. Org. Chem. 1994, 59, 5767.
| CrossRef | CAS |
[3]
P. E. Nielsen, M. Egholm, O. Buchardt, Bioconjug. Chem. 1994, 5, 3.
| CrossRef | CAS |
[4]
A. Ray, B. Norden, FASEB J. 2000, 14, 1041.
| CAS |
[5]
I. K. Cheah, S. S. Cheema, S. J. Langford, E. C. Lopes, K. J. Macfarlane, S. Petratos, B. J. Turner, Bioorg. Med. Chem. Lett. 2003, 13, 2377.
| CrossRef | CAS |
[6]
B. J. Turner, I. K. Cheah, K. J. Macfarlane, E. C. Lopes, S. Petratos, S. J. Langford, S. S. Cheema, J. Neurochem. 2003, 87, 752.
| CrossRef | CAS |
[7]
S. Pothukanuri, Z. Pianowski, N. Winssinger, Eur. J. Org. Chem. 2008, 3141.
| CrossRef | CAS |
[8]
S. A. Thomson, J. A. Josey, R. Cadilla, M. D. Gaul, C. Fred Hassman, M. J. Luzzio, A. J. Pipe, K. L. Reed, D. J. Ricca, R. W. Wiethe, S. A. Noble, Tetrahedron 1995, 51, 6179.
| CrossRef | CAS |
[9]
F. Wojciechowski, R. H. E. Hudson, J. Org. Chem. 2008, 73, 3807.
| CrossRef | CAS |
[10]
T. Stafforst, U. Diederichsen, Eur. J. Org. Chem. 2007, 681.
| CrossRef | CAS |
[11]
A. Porcheddu, G. Giacomelli, I. Piredda, M. Carta, G. Nieddu, Eur. J. Org. Chem. 2008, 5786.
| CrossRef | CAS |
[14]
Y.-q. Wu, D. C. Limburg, D. E. Wilkinson, M. J. Vaal, G. S. Hamilton, Tetrahedron Lett. 2000, 41, 2847.
| CrossRef | CAS |
[13]
A. H. St. Amant, R. H. E. Hudson, Org. Biomol. Chem. 2012, 10, 876.
| CrossRef | CAS |
[12]
J. M. Coull, M. Egholm, R. P. Hodge, M. Ismail, S. B. Rajur, PCT Patent WO 96/40685, 1996.
[15]
L. Bialy, J. J. Díaz-Mochón, E. Specker, L. Keinicke, M. Bradley, Tetrahedron 2005, 61, 8295.
| CrossRef | CAS |
[16]
R. H. E. Hudson, Y. Liu, F. Wojciechowski, Can. J. Chem. 2007, 85, 302.
| CrossRef |
[17]
X.-J. Liu, R.-Y. Chen, Phosphorus Sulfur 2001, 176, 19.
| CrossRef | CAS |
[18]
O. Seitz, O. Köhler, Chemistry 2001, 7, 3911.
| CrossRef | CAS |
[19]
D. V. Jarikote, O. Köhler, E. Socher, O. Seitz, Eur. J. Org. Chem. 2005, 15, 3187.
| CrossRef |
[20]
S. Chauhan, A. Varshney, B. Verma, M. Pennington, Tetrahedron Lett. 2007, 48, 4051.
| CrossRef | CAS |
[21]
W. L. F. Armarego, C. L. L. Chai, in Purification of Laboratory Chemicals (5th edn) 2003 (Elsevier: Cornwall).
[22]
D. Milic, M. Prato, Eur. J. Org. Chem. 2010, 476.
| CrossRef | CAS |
|
|
 |
Subscriber Login |
 |
|
e-Alerts
Connect with us
