PMID- 11695667
OWN - NLM
STAT- MEDLINE
DCOM- 20020226
LR  - 20190921
IS  - 0947-6539 (Print)
IS  - 0947-6539 (Linking)
VI  - 7
IP  - 20
DP  - 2001 Oct 15
TI  - Synthesis and thermodynamic studies of oligonucleotides containing the two 
      isomers of thymine glycol.
PG  - 4343-51
AB  - Thymine glycol is a major type of base damage, which is formed in DNA by reactive 
      oxygen species. I describe the synthesis of oligonucleotides containing the 5S 
      isomer of thymine glycol, which was not obtained by the oxidation of the 
      oligonucleotides. Before the 5S isomer was synthesized, a building block without 
      the protection of the tertiary hydroxy function at the C5 position of thymine 
      glycol was tested by the use of the previously reported 5R isomer. In the 
      presence of imidazole, migration of the silyl group between the C5 and C6 
      positions was observed, while the result of the oligonucleotide synthesis was 
      identical to the case of the fully protected building block. Therefore, 
      oligonucleotides containing the (5S)-thymine glycol were synthesized with the 
      disilylated building block. In contrast to the 5R derivative, two products were 
      detected in the HPLC analysis of the crude mixture after deprotection. Analysis 
      by matrix-assisted laser-desorption/ionization time-of-flight (MALDI-TOF) mass 
      spectrometry revealed that the larger peak was the desired oligonucleotide, and 
      it was found that the by-product was completely degraded by a short treatment 
      with ammonium hydroxide at room temperature. I also report the application of 
      oligonucleotides containing each isomer of thymine glycol to thermodynamic 
      analyses of base-pair formation. The thermodynamic parameters obtained for the 
      duplexes containing either the (5R)- or (5S)-thymine glycol indicated that the 
      thymine glycol cannot form a base-pair with any nucleobase, regardless of the 
      configuration at the C5 position.
FAU - Iwai, S
AU  - Iwai S
AD  - Department of Bioorganic Chemistry, Biomolecular Engineering Research Institute, 
      Suita, Osaka, Japan. iwai@chembio.t.u-tokyo.ac.jp
LA  - eng
PT  - Journal Article
PL  - Germany
TA  - Chemistry
JT  - Chemistry (Weinheim an der Bergstrasse, Germany)
JID - 9513783
RN  - 0 (Amides)
RN  - 0 (Oligonucleotides)
RN  - 0 (Phosphoric Acids)
RN  - 2943-56-8 (thymine glycol)
RN  - 9Q189608GB (phosphoramidic acid)
RN  - QR26YLT7LT (Thymine)
SB  - IM
MH  - Amides/chemistry
MH  - DNA Damage
MH  - Drug Stability
MH  - Nucleic Acid Denaturation
MH  - Nucleic Acid Hybridization
MH  - Oligonucleotides/*chemical synthesis/chemistry
MH  - Phosphoric Acids/chemistry
MH  - Stereoisomerism
MH  - Temperature
MH  - *Thermodynamics
MH  - Thymine/*analogs & derivatives/*chemistry
EDAT- 2001/11/07 10:00
MHDA- 2002/02/28 10:01
CRDT- 2001/11/07 10:00
PHST- 2001/11/07 10:00 [pubmed]
PHST- 2002/02/28 10:01 [medline]
PHST- 2001/11/07 10:00 [entrez]
AID - 10.1002/1521-3765(20011015)7:20<4343::AID-CHEM4343>3.0.CO;2-H [pii]
AID - 10.1002/1521-3765(20011015)7:20<4343::aid-chem4343>3.0.co;2-h [doi]
PST - ppublish
SO  - Chemistry. 2001 Oct 15;7(20):4343-51. doi: 
      10.1002/1521-3765(20011015)7:20<4343::aid-chem4343>3.0.co;2-h.