N-Benzoyl-protected Peptide Nucleic Acid (PNA) Monomers Expand the Range of Nucleobases Available for PNA-DNA Chimera

Masahito Inagaki; Ryohei Uematsu; Tatsuya Mizutani; Daisuke Unabara; Yasuyuki Araki; Seiji Sakamoto; Hiromu Kashida; Masaki Nishijima; Hiroyuki Asanuma; Yoshihisa Inoue; Takehiko Wada

doi:10.1246/cl.181048

N-Benzoyl-protected Peptide Nucleic Acid (PNA) Monomers Expand the Range of Nucleobases Available for PNA-DNA Chimera

Masahito Inagaki, Ryohei Uematsu, Tatsuya Mizutani, Daisuke Unabara, Yasuyuki Araki, Seiji Sakamoto, Hiromu Kashida, Masaki Nishijima, Hiroyuki Asanuma, Yoshihisa Inoue, Takehiko Wada

IMRAM - Division of Organic- and Biomaterials Research

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

Abstract

We synthesized N-benzoyl-protected peptide nucleic acid (PNA) monomers, which are robust under the conditions for deprotecting the 9-fluorenylmethoxycarbonyl (Fmoc) group by piperidine but are removable by aqueous ammonia and hence totally compatible with Fmoc-solid phase synthesis. This new invention expands the range of available nucleobase sequences, allowing us to use acid-sensitive PNA oligomers and purine nucleotides (both of which are difficult to use in the conventional methods) in the preparation of PNA-DNA chimeras to avoid the drawbacks of traditional PNAs.

Original language	English
Pages (from-to)	341-344
Number of pages	4
Journal	Chemistry Letters
Volume	48
Issue number	4
DOIs	https://doi.org/10.1246/cl.181048
Publication status	Published - 2019

Keywords

Benzoyl protecting group
PNA-DNA chimeras
Peptide nucleic acid (PNA)

Access to Document

10.1246/cl.181048

Cite this

@article{75b3978d9b68446dafa0cb5df27b091d,

title = "N-Benzoyl-protected Peptide Nucleic Acid (PNA) Monomers Expand the Range of Nucleobases Available for PNA-DNA Chimera",

abstract = "We synthesized N-benzoyl-protected peptide nucleic acid (PNA) monomers, which are robust under the conditions for deprotecting the 9-fluorenylmethoxycarbonyl (Fmoc) group by piperidine but are removable by aqueous ammonia and hence totally compatible with Fmoc-solid phase synthesis. This new invention expands the range of available nucleobase sequences, allowing us to use acid-sensitive PNA oligomers and purine nucleotides (both of which are difficult to use in the conventional methods) in the preparation of PNA-DNA chimeras to avoid the drawbacks of traditional PNAs.",

keywords = "Benzoyl protecting group, PNA-DNA chimeras, Peptide nucleic acid (PNA)",

author = "Masahito Inagaki and Ryohei Uematsu and Tatsuya Mizutani and Daisuke Unabara and Yasuyuki Araki and Seiji Sakamoto and Hiromu Kashida and Masaki Nishijima and Hiroyuki Asanuma and Yoshihisa Inoue and Takehiko Wada",

note = "Funding Information: We gratefully acknowledge the support of this work by a Grant-in-Aid for Scientific Research from JSPS and the Cooperative Research Programs “NJRC Mater. & Dev.” and “Dynamic Alliance”, both from MEXT. Publisher Copyright: {\textcopyright} 2019 The Chemical Society of Japan",

year = "2019",

doi = "10.1246/cl.181048",

language = "English",

volume = "48",

pages = "341--344",

journal = "Chemistry Letters",

issn = "0366-7022",

publisher = "The Chemical Society of Japan",

number = "4",

}

TY - JOUR

T1 - N-Benzoyl-protected Peptide Nucleic Acid (PNA) Monomers Expand the Range of Nucleobases Available for PNA-DNA Chimera

AU - Inagaki, Masahito

AU - Uematsu, Ryohei

AU - Mizutani, Tatsuya

AU - Unabara, Daisuke

AU - Araki, Yasuyuki

AU - Sakamoto, Seiji

AU - Kashida, Hiromu

AU - Nishijima, Masaki

AU - Asanuma, Hiroyuki

AU - Inoue, Yoshihisa

AU - Wada, Takehiko

N1 - Funding Information: We gratefully acknowledge the support of this work by a Grant-in-Aid for Scientific Research from JSPS and the Cooperative Research Programs “NJRC Mater. & Dev.” and “Dynamic Alliance”, both from MEXT. Publisher Copyright: © 2019 The Chemical Society of Japan

PY - 2019

Y1 - 2019

N2 - We synthesized N-benzoyl-protected peptide nucleic acid (PNA) monomers, which are robust under the conditions for deprotecting the 9-fluorenylmethoxycarbonyl (Fmoc) group by piperidine but are removable by aqueous ammonia and hence totally compatible with Fmoc-solid phase synthesis. This new invention expands the range of available nucleobase sequences, allowing us to use acid-sensitive PNA oligomers and purine nucleotides (both of which are difficult to use in the conventional methods) in the preparation of PNA-DNA chimeras to avoid the drawbacks of traditional PNAs.

AB - We synthesized N-benzoyl-protected peptide nucleic acid (PNA) monomers, which are robust under the conditions for deprotecting the 9-fluorenylmethoxycarbonyl (Fmoc) group by piperidine but are removable by aqueous ammonia and hence totally compatible with Fmoc-solid phase synthesis. This new invention expands the range of available nucleobase sequences, allowing us to use acid-sensitive PNA oligomers and purine nucleotides (both of which are difficult to use in the conventional methods) in the preparation of PNA-DNA chimeras to avoid the drawbacks of traditional PNAs.

KW - Benzoyl protecting group

KW - PNA-DNA chimeras

KW - Peptide nucleic acid (PNA)

UR - http://www.scopus.com/inward/record.url?scp=85065289310&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85065289310&partnerID=8YFLogxK

U2 - 10.1246/cl.181048

DO - 10.1246/cl.181048

M3 - Article

AN - SCOPUS:85065289310

SN - 0366-7022

VL - 48

SP - 341

EP - 344

JO - Chemistry Letters

JF - Chemistry Letters

IS - 4

ER -

N-Benzoyl-protected Peptide Nucleic Acid (PNA) Monomers Expand the Range of Nucleobases Available for PNA-DNA Chimera

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Cite this