Org Lett. 2005 Sep 29;7(20):4349-52.

A straightforward synthesis of 5'-peptide oligonucleotide conjugates using N(alpha)-Fmoc-protected amino acids.

Ocampo SM, Albericio F, Fernández I, Vilaseca M, Eritja R.

Source

Institut de Biologia Molecular de Barcelona, CSIC, Jordi Girona 18-26, E-08034 Barcelona, Spain.

Abstract

[reaction: see text] 5'-Peptide oligonucleotide conjugates were prepared stepwise on a single support using N(alpha)-Fmoc-protected amino acids and unprotected phosphate groups. The method uses commercially available reagents and is successful with most natural amino acids. The simplicity of the method may encourage researchers to prepare new oligonucleotide-peptide conjugates with novel properties.

PMID:: 16178530; [PubMed - indexed for MEDLINE]

Publication Types, MeSH Terms, Substances

Publication Types

Research Support, Non-U.S. Gov't

MeSH Terms

Substances

LinkOut - more resources

Full Text Sources

Other Literature Sources

Labome Expert Profile - Ramon Eritja - ExactAntigen/Labome

Supplemental Content

Save items

Related citations in PubMed

Synthesis of peptide-oligonucleotide phosphorothioate conjugates by convergent or stepwise solid-phase strategies. [Nucleosides Nucleotides Nuclei...]
Synthesis of peptide-oligonucleotide phosphorothioate conjugates by convergent or stepwise solid-phase strategies.
Antopolsky M, Azhayev A. Nucleosides Nucleotides Nucleic Acids. 2001 Apr-Jul; 20(4-7):539-50.
Preparation of oligonucleotide-peptide conjugates. [Bioconjug Chem. 1991]
Preparation of oligonucleotide-peptide conjugates.
Tung CH, Rudolph MJ, Stein S. Bioconjug Chem. 1991 Nov-Dec; 2(6):464-5.
Solid-phase synthesis of N-nosyl- and N-Fmoc-N-methyl-alpha-amino acids. [J Org Chem. 2007]
Solid-phase synthesis of N-nosyl- and N-Fmoc-N-methyl-alpha-amino acids.
Di Gioia ML, Leggio A, Liguori A, Perri F. J Org Chem. 2007 May 11; 72(10):3723-8. Epub 2007 Apr 17.
Review Design and synthesis of beta-peptides with biological activity. [Methods Mol Biol. 2006]
Review Design and synthesis of beta-peptides with biological activity.
Koyack MJ, Cheng RP. Methods Mol Biol. 2006; 340:95-109.
Review Urethane-protected alpha-amino acid N-carboxyanhydrides and peptide synthesis. [Biopolymers. 1996]
Review Urethane-protected alpha-amino acid N-carboxyanhydrides and peptide synthesis.
Fuller WD, Goodman M, Naider FR, Zhu YF. Biopolymers. 1996; 40(2):183-205.

See reviews... See all...

Cited by 2 PubMed Central articles

An activated triple bond linker enables 'click' attachment of peptides to oligonucleotides on solid support. [Nucleic Acids Res. 2011]
An activated triple bond linker enables 'click' attachment of peptides to oligonucleotides on solid support.
Wenska M, Alvira M, Steunenberg P, Stenberg A, Murtola M, Strömberg R. Nucleic Acids Res. 2011 Nov 1; 39(20):9047-59. Epub 2011 Jul 27.
Diels-Alder cycloadditions in water for the straightforward preparation of peptide-oligonucleotide conjugates. [Nucleic Acids Res. 2006]
Diels-Alder cycloadditions in water for the straightforward preparation of peptide-oligonucleotide conjugates.
Marchán V, Ortega S, Pulido D, Pedroso E, Grandas A. Nucleic Acids Res. 2006 Feb 14; 34(3):e24. Epub 2006 Feb 14.

Related information

Related Citations
Calculated set of PubMed citations closely related to the selected article(s) retrieved using a word weight algorithm. Related articles are displayed in ranked order from most to least relevant, with the “linked from” citation displayed first.
Substance (MeSH Keyword)
PubChem chemical substance (submitted) records that are classified under the same Medical Subject Headings (MeSH) controlled vocabulary as the current articles.
Cited in PMC
Full-text articles in the PubMed Central Database that cite the current articles.

Recent activity

Clear Turn Off Turn On

A straightforward synthesis of 5'-peptide oligonucleotide conjugates using N(alp...
A straightforward synthesis of 5'-peptide oligonucleotide conjugates using N(alpha)-Fmoc-protected amino acids.
Org Lett. 2005 Sep 29 ;7(20):4349-52.

PubMed
Evaluation of oral rabies vaccination programs for control of rabies epizootics ...
Evaluation of oral rabies vaccination programs for control of rabies epizootics in coyotes and gray foxes: 1995-2003.
J Am Vet Med Assoc. 2005 Sep 1 ;227(5):785-92.

PubMed
A 6-month clinical study assessing the safety and efficacy of two cetylpyridiniu...
A 6-month clinical study assessing the safety and efficacy of two cetylpyridinium chloride mouthrinses.
Am J Dent. 2005 Jul ;18 Spec No:24A-28A.

PubMed
Ocular effects of topical and systemic steroids.
Ocular effects of topical and systemic steroids.
Dermatol Clin. 1992 Jul ;10(3):505-12.

PubMed
Genome analysis and gene expression profiling of neuroblastoma and ganglioneurob...
Genome analysis and gene expression profiling of neuroblastoma and ganglioneuroblastoma reveal differences between neuroblastic and Schwannian stromal cells.
J Pathol. 2005 Nov ;207(3):346-57.

PubMed

Your browsing activity is empty.

Activity recording is turned off.

Turn recording back on

PubMed

Result Filters

Display Settings:

Send to: