Cross-coupling reactions of unprotected halopurine bases, nucleosides, nucleotides and nucleoside triphosphates with 4-boronophenylalanine in water. Synthesis of (purin-8-yl)- and (purin-6-yl)phenylalanines.
An expeditious and highly efficient single-step methodology for the introduction of a phenylalanine moiety into position 8 and 6 of the purine scaffold was developed based on aqueous-phase Pd-catalysed Suzuki-Miyaura cross-coupling reactions of unprotected 4-boronophenylalanine with 8-bromo- or 6-chloropurines. The scope of the methodology was demonstrated by syntheses of unprotected (adenin-8-yl)phenylalanine base, nucleosides, nucleotides and nucleoside triphosphates as well as (purin-6-yl)phenylalanine base and nucleosides. All these products were obtained in high yields and in optically pure form.
Capek
Petr
P
Centre for New Antivirals and Antineoplastics, Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, CZ-16610, Prague 6, Czech Republic.
Pohl
Radek
R
Hocek
Michal
M
D001880:Boranes / Q000737:chemistry*; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D011684:Purine Nucleosides / Q000737:chemistry*; D011685:Purine Nucleotides / Q000737:chemistry*; D011687:Purines / Q000138:chemical synthesis* / Q000737:chemistry
D001880:Boranes; D011684:Purine Nucleosides; D011685:Purine Nucleotides; D011687:Purines; D010649:Phenylalanine