Base-Pairing Properties of Double-Headed Nucleotides

Mick Hornum, Julie Stendevad, Pawan K. Sharma, Pawan Kumar, Rasmus B. Nielsen, Michael Petersen, Poul Nielsen*

*Kontaktforfatter for dette arbejde

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

Resumé

Nucleotides that contain two nucleobases (double-headed nucleotides) have the potential to condense the information of two separate nucleotides into one. This presupposes that both bases must successfully pair with a cognate strand. Here, double-headed nucleotides that feature cytosine, guanine, thymine, adenine, hypoxanthine, and diaminopurine linked to the C2′-position of an arabinose scaffold were developed and examined in full detail. These monomeric units were efficiently prepared by convergent synthesis and incorporated into DNA oligonucleotides by means of the automated phosphoramidite method. Their pairing efficiency was assessed by UV-based melting-temperature analysis in several contexts and extensive molecular dynamics studies. Altogether, the results show that these double-headed nucleotides have a well-defined structure and invariably behave as functional dinucleotide mimics in DNA duplexes.

OriginalsprogEngelsk
TidsskriftChemistry: A European Journal
Vol/bind25
Udgave nummer30
Sider (fra-til)7387-7395
ISSN0947-6539
DOI
StatusUdgivet - 28. maj 2019

Fingeraftryk

Base Pairing
Hypoxanthine
DNA
Guanine
Adenine
Molecular Dynamics Simulation
Freezing

Citer dette

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title = "Base-Pairing Properties of Double-Headed Nucleotides",
abstract = "Nucleotides that contain two nucleobases (double-headed nucleotides) have the potential to condense the information of two separate nucleotides into one. This presupposes that both bases must successfully pair with a cognate strand. Here, double-headed nucleotides that feature cytosine, guanine, thymine, adenine, hypoxanthine, and diaminopurine linked to the C2′-position of an arabinose scaffold were developed and examined in full detail. These monomeric units were efficiently prepared by convergent synthesis and incorporated into DNA oligonucleotides by means of the automated phosphoramidite method. Their pairing efficiency was assessed by UV-based melting-temperature analysis in several contexts and extensive molecular dynamics studies. Altogether, the results show that these double-headed nucleotides have a well-defined structure and invariably behave as functional dinucleotide mimics in DNA duplexes.",
keywords = "2,6-diaminopurine, double-headed nucleotides, hypoxanthine, oligonucleotides",
author = "Mick Hornum and Julie Stendevad and Sharma, {Pawan K.} and Pawan Kumar and Nielsen, {Rasmus B.} and Michael Petersen and Poul Nielsen",
year = "2019",
month = "5",
day = "28",
doi = "10.1002/chem.201901077",
language = "English",
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journal = "Chemistry: A European Journal",
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Base-Pairing Properties of Double-Headed Nucleotides. / Hornum, Mick; Stendevad, Julie; Sharma, Pawan K.; Kumar, Pawan; Nielsen, Rasmus B.; Petersen, Michael; Nielsen, Poul.

I: Chemistry: A European Journal, Bind 25, Nr. 30, 28.05.2019, s. 7387-7395.

Publikation: Bidrag til tidsskriftTidsskriftartikelForskningpeer review

TY - JOUR

T1 - Base-Pairing Properties of Double-Headed Nucleotides

AU - Hornum, Mick

AU - Stendevad, Julie

AU - Sharma, Pawan K.

AU - Kumar, Pawan

AU - Nielsen, Rasmus B.

AU - Petersen, Michael

AU - Nielsen, Poul

PY - 2019/5/28

Y1 - 2019/5/28

N2 - Nucleotides that contain two nucleobases (double-headed nucleotides) have the potential to condense the information of two separate nucleotides into one. This presupposes that both bases must successfully pair with a cognate strand. Here, double-headed nucleotides that feature cytosine, guanine, thymine, adenine, hypoxanthine, and diaminopurine linked to the C2′-position of an arabinose scaffold were developed and examined in full detail. These monomeric units were efficiently prepared by convergent synthesis and incorporated into DNA oligonucleotides by means of the automated phosphoramidite method. Their pairing efficiency was assessed by UV-based melting-temperature analysis in several contexts and extensive molecular dynamics studies. Altogether, the results show that these double-headed nucleotides have a well-defined structure and invariably behave as functional dinucleotide mimics in DNA duplexes.

AB - Nucleotides that contain two nucleobases (double-headed nucleotides) have the potential to condense the information of two separate nucleotides into one. This presupposes that both bases must successfully pair with a cognate strand. Here, double-headed nucleotides that feature cytosine, guanine, thymine, adenine, hypoxanthine, and diaminopurine linked to the C2′-position of an arabinose scaffold were developed and examined in full detail. These monomeric units were efficiently prepared by convergent synthesis and incorporated into DNA oligonucleotides by means of the automated phosphoramidite method. Their pairing efficiency was assessed by UV-based melting-temperature analysis in several contexts and extensive molecular dynamics studies. Altogether, the results show that these double-headed nucleotides have a well-defined structure and invariably behave as functional dinucleotide mimics in DNA duplexes.

KW - 2,6-diaminopurine

KW - double-headed nucleotides

KW - hypoxanthine

KW - oligonucleotides

U2 - 10.1002/chem.201901077

DO - 10.1002/chem.201901077

M3 - Journal article

VL - 25

SP - 7387

EP - 7395

JO - Chemistry: A European Journal

JF - Chemistry: A European Journal

SN - 0947-6539

IS - 30

ER -