TY - JOUR
T1 - Oxygen chiral phosphodiesters-8. Stereochemical course of the base-catalyzed hydrolysis of cyclic 2'-deoxyadenosine 3',5'-[17O, 18O]monophosphate
AU - Mehdi, Shujaath
AU - Coderre, Jeffrey A.
AU - Gerlt, John A.
N1 - Funding Information:
AckN~wledge~nrs-Thhei ghfield “P NMR spectras hown in thef iguresw ereo btaineda t WesleyanU niversityw ith the generousa ssistanceo f Prof. Philip Boiton. This research was supportedb y a grant from the National Instituteso f Health (GM-22350).
PY - 1983
Y1 - 1983
N2 - At 100° and in 0.2 M Ba(OH)2 the Rp diastereomer of cyclic 2'-deoxyadenosine 3',5' -[17O, 18O]monophosphate is hydrolyzed to a 4:1 mixture of the Sp diastereomer of 3' -[16O, 17O, 18O]dAMP and the Rp diastereomer of 5' -[16O, 17O, 18O]dAMP, respectively, demonstrating that the hydrolysis reaction is accompanied by complete inversion of configuration at phosphorus. This finding establishes that pseudorotation of pentacoordinate reaction intermediates is unimportant in this chemical hydrolysis reaction.
AB - At 100° and in 0.2 M Ba(OH)2 the Rp diastereomer of cyclic 2'-deoxyadenosine 3',5' -[17O, 18O]monophosphate is hydrolyzed to a 4:1 mixture of the Sp diastereomer of 3' -[16O, 17O, 18O]dAMP and the Rp diastereomer of 5' -[16O, 17O, 18O]dAMP, respectively, demonstrating that the hydrolysis reaction is accompanied by complete inversion of configuration at phosphorus. This finding establishes that pseudorotation of pentacoordinate reaction intermediates is unimportant in this chemical hydrolysis reaction.
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U2 - 10.1016/S0040-4020(01)88658-0
DO - 10.1016/S0040-4020(01)88658-0
M3 - Article
AN - SCOPUS:0345314504
SN - 0040-4020
VL - 39
SP - 3483
EP - 3492
JO - Tetrahedron
JF - Tetrahedron
IS - 21
ER -