Total synthesis of proximicin A-C and synthesis of new furan-based DNA binding agents.
The total synthesis of the natural occurring polyamides proximicin A-C (3-5) has been accomplished. A short and efficient synthesis of a thus far unknown 4-amino-2-furan carboxylic acid was developed. Furthermore, this unique heterocyclic gamma-amino-acid was used for the synthesis of a new class of AT-selective DNA-binding agents derived from the natural products combining structural features of the proximicins with those from the known DNA-binding natural products netropsin (1) and distamycin (2).
Wolter
Falko E
FE
Institut für Chemie, TU Berlin, Strasse des 17. Juni 124, 10623 Berlin, Germany.
Schneider
Kathrin
K
Davies
Brian P
BP
Socher
Elke R
ER
Nicholson
Graeme
G
Seitz
Oliver
O
Süssmuth
Roderich D
RD
D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry; D004247:DNA / Q000737:chemistry* / Q000378:metabolism; D004214:Distamycins / Q000737:chemistry / Q000494:pharmacology; D005663:Furans / Q000737:chemistry*; D015394:Molecular Structure; D009429:Netropsin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D009757:Nylons / Q000138:chemical synthesis* / Q000737:chemistry
D000596:Amino Acids; D004214:Distamycins; D005663:Furans; D009757:Nylons; C529559:proximicin A; C529560:proximicin B; C529561:proximicin C; D009429:Netropsin; C030000:stallimycin; D004247:DNA; C039281:furan