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Chemo‐Enzymatic Synthesis of Thymidine 13 C‐Labelled in the 2′‐Deoxyribose Moiety
Author(s) -
Ouwerkerk Niels,
van Boom Jacques H.,
Lugtenburg Johan,
Raap Jan
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(200003)2000:5<861::aid-ejoc861>3.0.co;2-e
Subject(s) - chemistry , deoxyribose , aldolase a , dihydroxyacetone , moiety , triosephosphate isomerase , dihydroxyacetone phosphate , stereochemistry , yield (engineering) , borohydride , nucleoside , furanose , enzyme , nucleic acid , ring (chemistry) , biochemistry , organic chemistry , catalysis , materials science , glycerol , metallurgy
Abstract A synthesis of [3′,4′‐ 13 C 2 ]thymidine ( 1 ) is described in which [ 13 C 2 ]acetic acid ( 2 ) is converted into the nucleoside in twelve steps with 9% overall yield. D ‐2‐Deoxyribose‐5‐phosphate aldolase (DERA, EC 4.1.2.4) and triosephosphate isomerase (TPI, EC 5.3.1.1) are used for the stereocontrolled formation of D ‐[3,4‐ 13 C 2 ]‐2‐deoxyribose‐5‐phosphate ( 8 ) from [2,3‐ 13 C 2 ]dihydroxyacetone monophosphate (DHAP, 7 ) and acetaldehyde in 80% yield. The route permits the introduction of isotopically enriched carbon atoms at any position or combination of positions in the furanose ring and the product can be coupled with any of the four naturally occurring base moieties.