Premium
Synthesis of the Anticodon Hairpin t RNA f Met Containing N ‐{[9‐( β ‐ D ‐Ribofuranosyl)‐9 H ‐purin‐6‐yl]carbamoyl}‐ L ‐threonine (= N 6 ‐{{[(1 S ,2 R )‐1‐Carboxy‐2‐hydroxypropyl]amino}carbonyl}adenosine, t 6 A)
Author(s) -
Boudou Valerie,
Langridge James,
Van Aerschot Arthur,
Hendrix Chris,
Millar Alan,
Weiss Patrick,
Herdewijn Piet
Publication year - 2000
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/(sici)1522-2675(20000119)83:1<152::aid-hlca152>3.0.co;2-1
Subject(s) - chemistry , moiety , ribonucleotide , threonine , stereochemistry , transfer rna , uracil , protecting group , hydrolysis , adenosine , rna , nucleotide , organic chemistry , biochemistry , phosphorylation , serine , alkyl , gene , dna
As part of our studies on the structure of yeast t RNA f Met , we investigated the incorporation of N ‐{[9‐( β ‐ D ‐ribofuranosyl)‐9 H ‐purin‐6‐yl]carbamoyl}‐ L ‐threonine (t 6 A) in the loop of a RNA 17‐mer hairpin. The carboxylic function of the L ‐threonine moiety of t 6 A was protected with a 2‐(4‐nitrophenyl)ethyl group, and a ( tert ‐butyl)dimethylsilyl group was used for the protection of its secondary OH group. The 2′‐OH function of the standard ribonucleotide building blocks was protected with a [(triisopropylsilyl)oxy]methyl group. Removal of the base‐labile protecting groups of the final RNA with 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) and then with MeNH 2 was done under carefully controlled conditions to prevent hydrolysis of the carbamate function, leading to loss of the L ‐threonine moiety.