Stepwise Solid-Phase Synthesis of Peptide-Oligonucleotide Conjugates on New Solid Supports

Antopolsky, Maxim; Azhayev, Alex

doi:10.1002/(sici)1522-2675(19991215)82:12<2130::aid-hlca2130>3.0.co;2-a

Cited by 30 publications

(23 citation statements)

References 11 publications

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“…3 a). They might be obtained either by ligation of two alanyl-PNA fragments to the 3′- and 5′-termini of the DNA single strand, respectively, (Ede et al 1994 ; Arar et al 1995 ; Vives and Lebleu 1997 ; Harrison and Balasubramanian 1998 ; McMinn and Greenberg 1999 ; Forget et al 2001 ; Zatsepin et al 2002 ; Ollivier et al 2002 ) or by solid phase synthesis of the whole chimeric strand under DNA synthesis conditions (Bergmann and Bannwarth 1995 ; Truffert et al 1996 ; Antopolsky and Azhayev 1999 , 2000 ; Sakakura and Hayakawa 2000 ; Antopolsky et al 2002 ; Stetsenko et al 2002 ; Musumeci et al 2004 ). Uhlmann and van Boom already reported the stepwise solid phase synthesis of aminoethylglycine-PNA/DNA-chimera (Fig.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of novel MMT/acyl-protected nucleo alanine monomers for the preparation of DNA/alanyl-PNA chimeras

et al. 2009

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Alanyl-peptide nucleic acid (alanyl-PNA)/DNA chimeras are oligomers envisaged to be beneficial in efficient DNA diagnostics based on an improved molecular beacon concept. A synthesis of alanyl-PNA/DNA chimera can be based on the solid phase assembly of the oligomer with mixed oligonucleotide/peptide backbone under DNA synthesis conditions, in which the nucleotides are introduced as phosphoramidites, whereas the nucleo amino acids make use of the acid labile monomethoxytrityl (MMT) group for temporary protection of the α-amino groups and acyl protecting groups for the exocyclic amino functions of the nucleobases. In this work, we realized for the first time the synthesis of all four MMT/acyl-protected nucleo alanines, achieved by deprotection/reprotection of the newly synthesized Boc/acyl intermediates, useful monomers for the obtainment of (alanyl-PNA)/DNA chimeras by conditions fully compatible with the standard phosphoramidite DNA synthesis strategy.

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Section: Resultsmentioning

confidence: 99%

Synthesis of novel MMT/acyl-protected nucleo alanine monomers for the preparation of DNA/alanyl-PNA chimeras

et al. 2009

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“…First a base-labile branched anchor-linker is coupled to the solid support. The linker carries a primary hydroxyl group protected by dimethoxytrityl, as well as a second functionality, usually a Fmoc-protected amino group [26][27][28][29][30][31][32] (Fig. ( 3)).…”

Section: Synthetic Methodologiesmentioning

confidence: 99%

Conjugates of Oligonucleotides and Analogues with Cell Penetrating Peptides as Gene Silencing Agents

Zatsepin¹,

Turner²,

Oretskaya³

et al. 2005

CPD

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The review describes key aspects of the synthesis and biological activities of conjugates of oligonucleotides and their analogues with synthetic peptides, in particular aimed towards gene silencing applications. The common methods of synthesis of oligonucleotide-peptide conjugates (OPCs) and PNA-peptide conjugates (PPCs) are described, which include both total solid-phase and fragment coupling approaches. In addition, various applications of conjugates as gene silencing agents are outlined. These include antisense and steric block applications in mammalian cells of OPCs, PPCs and phosphorodiamidate morpholinooligonucleotide (PMO)-peptide conjugates, gene silencing in bacteria, various DNA targeting applications, and recent reports of gene silencing activities of siRNA-peptide conjugates. A table listing all peptides used as oligonucleotide conjugates for gene silencing applications is also included.

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“…Conjugations using this method primarily link the 3' end of an oligonucleotide to the N-terminus of the peptide [22,[24][25][26][27]. However, the 3' terminus of an oligonucleotide has been conjugated to the C-terminus of a peptide [28], and 5' peptide-oligonucleotide hybrids have also been prepared [29]. While conjugation to the 3' end of the oligonucleotide provides nuclease resistance, additional protection from degradation can be conferred through linkage to a D-peptide, which engenders protection against the action of cellular proteases [30].…”

Section: (Ii) Total Stepwise Solid-phase Approachmentioning

confidence: 99%

Peptide-Oligonucleotide Hybrids in Antisense Therapy

Pierce

White

Tregear

et al. 2005

MRMC

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Antisense technology provides outstanding promise for treatment of human disease, having broad applicability and high specificity. Although advances have been made in antisense oligonucleotide chemistry, leading to increased plasma and cellular stability, and decreased toxicity, considerable potential remains for the enhancement of oligonucleotide uptake for targeted delivery of oligonucleotides. One promising avenue for achieving this is via linkage of antisense oligonucleotides to peptide carriers. This review looks at the current status of developments in this area.

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Stepwise Solid-Phase Synthesis of Peptide-Oligonucleotide Conjugates on New Solid Supports

Cited by 30 publications

References 11 publications

Synthesis of novel MMT/acyl-protected nucleo alanine monomers for the preparation of DNA/alanyl-PNA chimeras

Synthesis of novel MMT/acyl-protected nucleo alanine monomers for the preparation of DNA/alanyl-PNA chimeras

Conjugates of Oligonucleotides and Analogues with Cell Penetrating Peptides as Gene Silencing Agents

Peptide-Oligonucleotide Hybrids in Antisense Therapy

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