Biomimetic synthesis of the IDO inhibitors exiguamine A and B.
Biomimetic synthesis is an attempt to assemble natural products along biosynthetic lines without recourse to the full enzymatic machinery of nature. We exemplify this with a total synthesis of exiguamine A and the newly isolated natural product exiguamine B. The most noteworthy feature of this work is an oxidative endgame drawing from the complex chemistry of catecholamines, which allows for ready access to a new class of nanomolar indoleamine-2,3-dioxygenase inhibitors.
Volgraf
Matthew
M
Department of Chemistry, University of California, Berkeley, California 94720, USA.
Lumb
Jean-Philip
JP
Brastianos
Harry C
HC
Carr
Gavin
G
Chung
Marco K W
MK
Münzel
Martin
M
Mauk
A Grant
AG
Andersen
Raymond J
RJ
Trauner
Dirk
D
D040761:Biomimetic Materials / Q000138:chemical synthesis* / Q000737:chemistry; D002395:Catecholamines / Q000096:biosynthesis / Q000138:chemical synthesis / Q000737:chemistry; D003500:Cyclization; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D050503:Indoleamine-Pyrrole 2,3,-Dioxygenase / Q000037:antagonists & inhibitors*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011809:Quinones / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D002395:Catecholamines; D004791:Enzyme Inhibitors; D026121:Indole Alkaloids; D050503:Indoleamine-Pyrrole 2,3,-Dioxygenase; D007211:Indoles; D011809:Quinones; D013141:Spiro Compounds; C516830:exiguamine A; C531460:exiguamine B