Skip to main content
Nucleic Acids Research logoLink to Nucleic Acids Research
. 1974 Feb;1(2):223–234. doi: 10.1093/nar/1.2.223

Studies on transfer ribonucleic acids and related compounds. VIII(1). Further studies on aromatic phosphoramidates as a protecting group for phosphomonoesters

E Ohtsuka 1, A Honda 1, H Shigyo 1, S Morioka 1, T Sugiyama 1, M Ikehara 1
PMCID: PMC343341  PMID: 4415960

Abstract

Stability of aromatic phosphoramidates was studied using 2′,3′-O-dibenzoyluridine 5′-phosphoramidates and N,2′,3′-O-tribenzoylcytidine 5′-phosphate. The effect of dicyclohexylcarbodiimide in this mixture was investigated. Decomposition of the anilidate was slower in the presence of DCC.

Substituted anilidates of uridine 5′-phosphate were synthesized and the stability of these amidates in anhydrous pyridine was studied.

2′-O-Benzoyluridine 3′-phosphoranilidate and the corresponding β-naphthylidate were compared in their stabilities in anhydrous pyridine, 50% aqueous pyridine and 80% acetic acid. 2′-O-Benzoyluridine 3′-phosphoro-β-naphthylidate was used for synthesis of dinucleotides.

Full text

PDF
223

Selected References

These references are in PubMed. This may not be the complete list of references from this article.

  1. Agarwal K. L., Yamazaki A., Khorana H. G. Studies on polynucleotides. 98. A convenient and general method for the preparation of protected dideoxyribonucleotides containing 5'-phosphate end groups. J Am Chem Soc. 1971 Jun 2;93(11):2754–2762. doi: 10.1021/ja00740a028. [DOI] [PubMed] [Google Scholar]
  2. Allen R. J. The estimation of phosphorus. Biochem J. 1940 Jun;34(6):858–865. doi: 10.1042/bj0340858. [DOI] [PMC free article] [PubMed] [Google Scholar]
  3. Ohtsuka E., Murao K., Ubasawa M., Ikehara M. A new method for the synthesis of protected ribooligonucleotides with 3'-phosphate end groups. J Am Chem Soc. 1969 Mar 12;91(6):1537–1538. doi: 10.1021/ja01034a047. [DOI] [PubMed] [Google Scholar]
  4. Otsuka E., Ubasawa M., Morioka S., Ikehara M. Studies on transfer ribonucleic acids and related compounds. VI. Synthesis of yeast alanine transfer ribonucleic acid 3'-terminal nonanucleotides and 5'-terminal hexanucleotides. J Am Chem Soc. 1973 Jul 11;95(14):4725–4733. doi: 10.1021/ja00795a042. [DOI] [PubMed] [Google Scholar]

Articles from Nucleic Acids Research are provided here courtesy of Oxford University Press

RESOURCES