Design, synthesis, and biological evaluation of potent discodermolide fluorescent and photoaffinity molecular probes.
[structure: see text] The design, synthesis, and biological evaluation of a series of (+)-discodermolide molecular probes possessing photoaffinity and fluorescent appendages has been achieved. Stereoselective olefin cross-metathesis comprised a key tactic for construction of two of the molecular probes. Three photoaffinity probes were radiolabeled with tritium.
Smith
Amos B
AB
Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104, USA. smithab@sas.upenn.edu
Rucker
Paul V
PV
Brouard
Ignacio
I
Freeze
B Scott
BS
Xia
Shujun
S
Horwitz
Susan Band
SB
D000473:Alkanes / Q000138:chemical synthesis / Q000737:chemistry; D001577:Benzophenones / Q000737:chemistry; D002219:Carbamates / Q000138:chemical synthesis / Q000737:chemistry; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis / Q000737:chemistry; D015335:Molecular Probes / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D019920:Photoaffinity Labels / Q000138:chemical synthesis / Q000737:chemistry; D011753:Pyrones / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D000473:Alkanes; D001577:Benzophenones; D002219:Carbamates; D005456:Fluorescent Dyes; D007783:Lactones; D015335:Molecular Probes; D019920:Photoaffinity Labels; D011753:Pyrones; C071229:discodermolide