The synthesis of polyamide nucleic acids using a novel monomethoxytrityl protecting-group strategy

Will, David W.; Breipohl, Gerhard; Langner, Dietrich; Knolle, Jochen; Uhlmann, Eugen

doi:10.1016/0040-4020(95)00766-2

Cited by 106 publications

(130 citation statements)

References 11 publications

Supporting

Mentioning

112

Contrasting

Unclassified

Order By: Relevance

“…amination with glycine esters and protected aminoacetaldehyde [23,24] ( Figure 2B), and reductive amination using 1,2-diaminoethane and glyoxylic acid [25,26] ( Figure 2C). Further reaction steps lead to protected aminoethylglycine derivatives with unprotected secondary amino groups to which the nucleobase acetic acid derivatives can be coupled.…”

Section: Pna Monomeric Building Blocks With An Aminoethylglycine Backmentioning

confidence: 98%

“…B) Synthesis of Boc ± Aeg derivates by reductive amination from Boc-aminoacetaldehyde and glycine esters. C) Synthesis of Aeg derivates by reductive amination from 1,2-diaminoethane and glyoxylic acid: [25,26] a) H 2 /Pd/C, H 2 O; b) MeOH/HCl; c) Mmt-Cl, DMF, NEt 3 ; d) Fmoc-(ONSu), dioxane/H 2 O; e) MeOH/HCl.…”

Section: Pna Monomeric Building Blocks With An Aminoethylglycine Backmentioning

confidence: 99%

See 1 more Smart Citation

PNA: Synthetic Polyamide Nucleic Acids with Unusual Binding Properties

Uhlmann¹,

Peyman²,

Breipohl³

et al. 1998

Angewandte Chemie International Edition

Self Cite

397

217

View full text Add to dashboard Cite

The astonishing discovery that peptide nucleic acids (PNAs, B=nucleobase), in spite of their drastic structural difference to natural DNA, are better nucleic acid mimetics than many other oligonucleotides has resulted in an explosion of research into this class of compounds. The synthesis, physical properties, and biological interactions of PNAs as well as their chimeras with DNA and RNA are summarized here.

show abstract

Section: Pna Monomeric Building Blocks With An Aminoethylglycine Backmentioning

confidence: 98%

Section: Pna Monomeric Building Blocks With An Aminoethylglycine Backmentioning

confidence: 99%

PNA: Synthetic Polyamide Nucleic Acids with Unusual Binding Properties

Uhlmann¹,

Peyman²,

Breipohl³

et al. 1998

Angewandte Chemie International Edition

Self Cite

397

217

View full text Add to dashboard Cite

show abstract

“…[15] This methodology was chosen because of its mild deprotection chemistry and its compatibility with DNA synthesis.…”

Section: Sections Of the Chemical Structures Of Deoxyribonucleic Acidmentioning

confidence: 99%

Olefinic Peptide Nucleic Acids (OPAs): New Aspects of the Molecular Recognition of DNA by PNA

Schütz

Cantin

Roberts

et al. 2000

Angew. Chem. Int. Ed.

Self Cite

View full text Add to dashboard Cite

Vive la différence! Replacement of the base‐linker amide functionality in peptide nucleic acids (PNAs) by an isostructural C−C double bond (shown schematically) leads to a dramatic change in DNA affinity, preferred strand orientation, and triplex‐forming properties, and thus highlights the importance of electrostatic properties over geometric properties of the amide functionality in PNA/DNA recognition.

show abstract

“…The protective groups of the side chain of the amino acids (Fmoc for Lys and Fm for Asp) and the linker of the first aminoacid to the support were base-labile so that they would be removed at the same time as the protective groups of the nucleobases. To this end, the 6-aminohexylsuccinyl (AmHex, [34]) was used. This linker yields the peptide with an aminohexylamide group at the C-terminal.…”

Section: Synthesis Of Oligonucleotide-peptide Conjugatesmentioning

confidence: 99%