Solution-phase synthesis of nucleobase-substituted analogues of triostin A.
A synthesis of novel analogues of triostin A presenting two identical or different nucleobases instead of the original quinoxaline substituents has been developed. The DNA bisintercalator triostin A (1) with its rigid backbone provides an optimal scaffold for a parallel preorganization of the intercalating moieties. The bicyclic octadepsipeptide is built up stepwise in solution and modified with various nucleobase-substituted acetic acids at a late stage. The choice of orthogonal protecting groups allows for the synthesis of triostin analogues bearing two different substituents.
Lorenz
Katrin B
KB
Institut für Organische und Biomolekulare Chemie, Georg-August-Universität Göttingen, Tammannstrasse 2, D-37077 Goettingen, Germany.
Diederichsen
Ulf
U
D004247:DNA / Q000737:chemistry; D009711:Nucleotides / Q000737:chemistry*; D011810:Quinoxalines / Q000138:chemical synthesis* / Q000737:chemistry; D012996:Solutions
D009711:Nucleotides; D011810:Quinoxalines; D012996:Solutions; C031945:triostin A; C017738:TANDEM (quinoxaline); D004247:DNA