Coupling strategies for the synthesis of peptide-oligonucleotide conjugates for patterned synthetic biomineralization

Journal of Nucleic Acids

Volumn 2011, Issue , 2011, Pages

  Carter, Joshua D ^a   LaBean, Thomas H ^a,b  

^a DUKE UNIVERSITY   (United States)

^b Duke University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

(BENZOTRIAZOL 1 YLOXY)TRIPYRROLIDINOPHOSPHONIUM HEXAFLUOROPHOSPHATE; 1 (3 DIMETHYLAMINOPROPYL) 3 ETHYLCARBODIIMIDE; 4 (4,6 DIMETHOXY[1,3,5]TRIAZIN 2 YL) 4 METHYLMORPHOLINIUM CHLORIDE; AMINO ACID; DNA; GOLD; N,N DIMETHYLFORMAMIDE; O BENZOTRIAZOLE N,N,N',N' TETRAMETHYLURONIUM HEXAFLUOROPHOSPHATE; OLIGONUCLEOTIDE; PEPTIDE; REAGENT; SEPHAROSE; UNCLASSIFIED DRUG; WATER;

AMINO TERMINAL SEQUENCE; ARTICLE; ATOMIC FORCE MICROSCOPY; BIOMINERALIZATION; CARBOXY TERMINAL SEQUENCE; CHEMICAL BINDING; CHEMICAL REACTION; COMBINATORIAL LIBRARY; GEL ELECTROPHORESIS; IMMOBILIZATION; MASS SPECTROMETRY; MOLECULAR GENETICS; NUCLEOTIDE METABOLISM; PEPTIDE SYNTHESIS; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; PROTEIN ASSEMBLY; PROTEIN DNA INTERACTION; PROTEIN PROTEIN INTERACTION; SOLID;

EID: 84862210401     PISSN: 20900201     EISSN: 2090021X     Source Type: Journal    
DOI: 10.4061/2011/926595     Document Type: Article

References (23)

1. Stephenson M. L., Zamecnik P. C., Inhibition of Rous sarcoma viral RNA translation by a specific oligodeoxyribonucleotide. Proceedings of the National Academy of Sciences of the United States of America 1978 75 1 285 288 2-s2.0-0005772676 (Pubitemid 8290784)
2. Zamecnik P. C., Stephenson M. L., Inhibition of Rous sarcoma virus replication and cell transformation by a specific oligodeoxynucleotide. Proceedings of the National Academy of Sciences of the United States of America 1978 75 1 280 284 2-s2.0-0041582974 (Pubitemid 8290783)
3. Oehlke J., Wallukat G., Wolf Y., Ehrlich A., Wiesner B., Berger H., Bienert M., Enhancement of intracellular concentration and biological activity of PNA after conjugation with a cell-penetrating synthetic model peptide. European Journal of Biochemistry 2004 271 14 3043 3049 2-s2.0-3242798141 10.1111/j.1432-1033.2004.04236.x (Pubitemid 38980289)
4. Wilson D. S., Szostak J. W., In vitro selection of functional nucleic acids. Annual Review of Biochemistry 1999 68 611 647 2-s2.0-0032853242 10.1146/annurev.biochem.68.1.611 (Pubitemid 29449205)
5. 125I-labeled triplex-forming oligonucleotides conjugated with nuclear localization signal peptide. Antisense and Nucleic Acid Drug Development 2002 12 1 43 49 2-s2.0-0036236762 (Pubitemid 34461542)
6. Sarikaya M., Tamerler C., Jen A. K. Y., Schulten K., Baneyx F., Molecular biomimetics: nanotechnology through biology. Nature Materials 2003 2 9 577 585 2-s2.0-0141780801 10.1038/nmat964
7. Cha J. N., Stucky G. D., Morse D. E., Deming T. J., Biomimetic synthesis of ordered silica structures mediated by block copolypeptides. Nature 2000 403 6767 289 292 2-s2.0-0034688280 10.1038/35002038 (Pubitemid 30062380)
8. Samano E. C., samano@cnyn.unam.mx Pilo-Pais M., Goldberg S., Vogen B. N., Finkelstein G., LaBean T. H., thomas.labean@duke.edu Self-assembling DNA templates for programmed artificial biomineralization. Soft Matter 2011 7 7 3240 3245 10.1039/c0sm01318h
9. Yan H., Park S. H., Finkelstein G., Reif J. H., LaBean T. H., DNA-templated self-assembly of protein arrays and highly conductive nanowires. Science 2003 301 5641 1882 1884 2-s2.0-0141534348 10.1126/science.1089389 (Pubitemid 37221388)
10. Li H., Carter J. D., LaBean T. H., Nanofabrication by DNA self-assembly. Materials Today 2009 12 5 20 28 2-s2.0-65649141581 10.1016/S1369-7021(09)70157-9
11. Seeman N. C., DNA in a material world. Nature 2003 421 6921 427 431 2-s2.0-0037461742 10.1038/nature01406 (Pubitemid 36157949)
12. Carter J. D., Labean T. H., thomas.labean@duke.edu Organization of inorganic nanomaterials via programmable DNA self-assembly and peptide molecular recognition. ACS Nano 2011 5 3 2200 2205 10.1021/nn1033983
13. Tung C. H., Stein S., Preparation and applications of peptide-oligonucleotide conjugates. Bioconjugate Chemistry 2000 11 5 605 618 2-s2.0-0033799686 10.1021/bc0000334
14. Venkatesan N., Kim B. H., Peptide conjugates of oligonucleotides: synthesis and applications. Chemical Reviews 2006 106 9 3712 3761 2-s2.0-33749823347 10.1021/cr0502448 (Pubitemid 44560455)
15. Hnilova M., Oren E. E., Seker U. O. S., Wilson B. R., Collino S., Evans J. S., Tamerler C., Sarikaya M., Effect of molecular conformations on the adsorption behavior of gold-binding peptides. Langmuir 2008 24 21 12440 12445 2-s2.0-56449087021 10.1021/la801468c
16. Halpin D. R., Lee J. A., Wrenn S. J., Harbury P. B., DNA display III. Solid-phase organic synthesis on unprotected DNA. PLoS Biology 2004 2 7 E175 2-s2.0-19344370973 10.1371/journal.pbio.0020175 (Pubitemid 39234415)
17. Taton T. A., Preparation of gold nanoparticle-DNA conjugates. Current Protocols in Nucleic Acid Chemistry 2002 12 2 11 2-s2.0-44249124790
18. Viladkar S. M., Guanine rich oligonucleotide-amino acid/peptide conjugates: preparation and characterization. Tetrahedron 2002 58 3 495 502 2-s2.0-0037074220 10.1016/S0040-4020(01)01158-9 (Pubitemid 34075577)
19. Hojo K., Maeda M., Tanakamaru N., Mochida K., Kawasaki K., Solid phase peptide synthesis in water VI: evaluation of water-soluble coupling reagents for solid phase peptide synthesis in aqueous media. Protein and Peptide Letters 2006 13 2 189 192 2-s2.0-33646430621 10.2174/092986606775101607
20. Kunishima M., Kawachi C., Morita J., Terao K., Iwasaki F., Tani S., 4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride: an efficient condensing agent leading to the formation of amides and esters. Tetrahedron 1999 55 46 13159 13170 2-s2.0-0033550301 10.1016/S0040-4020(99)00809-1 (Pubitemid 29502265)
21. Harris D. C., Chu X., Jayawickramarajah J., DNA-small molecule chimera with responsive protein-binding ability. Journal of the American Chemical Society 2008 130 45 14950 14951 2-s2.0-57349129001 10.1021/ja806552c
22. Zhang J., Liu Y., Ke Y., Yan H., Periodic square-like gold nanoparticle arrays templated by self-assembled 2D DNA nanogrids on a surface. Nano Letters 2006 6 2 248 251 2-s2.0-33644905342 10.1021/nl052210l (Pubitemid 43382961)
23. Peyrottes S., Mestre B., Burlina F., Gait M. J., The synthesis of peptide-oligonucleotide conjugates by a fragment coupling approach. Tetrahedron 1998 54 41 12513 12522 2-s2.0-0032497680 (Pubitemid 28552691)