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'Cyclic Phosphate as Protection Group' in keywords Facet   section ZfN Section C  [X]
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1980 (1)
1Author    C. Sauer, U. SchwabeRequires cookie*
 Title    M ethod for the Selective 2 '-0 -S u b stitu tio n o f N ucleosides  
 Abstract    This paper presents a new method for selective reactions o f predetermined sugar hydroxyls o f nucleosides. Suc-cinylated nucleosides were investigated as examples for the use of the cyclic phosphate group for protecting purposes. Starting from cyclic AMP the 2'-0-group was selectively succinylated yielding 93% 2'-0-succinyl cyclic AMP. The cyclic phosphate was enzymatically dephosphorylated in a one step procedure under neutral conditions and 2 '-0 -suc-cinyl adenosine containing a small amount o f the 3'-0-isomer was produced in 91% yield. When establishment of equilibrium of the 2'-0-and 3'-0-isomers was allowed, 54% yield of crystallized 3'-0-succinyl adenosine was prod­ uced. The results suggest that the easily accessible cyclic monophosphates are good protecting groups for the pro­ duction of nucleoside derivatives, especially at the 2 '-0 -position under neutral conditions. 
  Reference    Z. Naturforsch. 35c, 163—167 (1980); received June 15/September 21 1979 
  Published    1980 
  Keywords    Cyclic AMP, Enzymatic Synthesis, Cyclic Phosphate as Protection Group, 2'-0-Succinyl Adenosine, 2'-0-Substitu-tion o f Nucleosides 
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 TEI-XML for    default:Reihe_C/35/ZNC-1980-35c-0163_n.pdf 
 Identifier    ZNC-1980-35c-0163_n 
 Volume    35