Approaches for the synthesis of functionalized cryptophycins.
The first syntheses of bioactive cryptophycins functionalized at unit D were accomplished in a one-pot Staudinger reduction/cyclization step. An azido precursor for the lower part of the backbone was introduced to minimize protective group chemistry and enable a very convenient synthesis of cryptophycin-52 and unit D cryptophycin analogues containing an ester or a free carboxylic acid for bioconjugations. Both new cryptophycin derivatives show high biological activity in cytotoxicity assays.
Sammet
Benedikt
B
Department of Chemistry, Organic and Bioorganic Chemistry, Bielefeld University, Universitätsstrasse 25, 33615 Bielefeld, Germany.
Bogner
Tobias
T
Nahrwold
Markus
M
Weiss
Christine
C
Sewald
Norbert
N
D047630:Depsipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D047630:Depsipeptides; C088419:cryptophycin