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  • Title: Crystallographic determination of stereochemistry of biologically active 2'',3''-dibromo-7-epi-10-deacetylcephalomannine.
    Author: Jiang Y, Lin HX, Chen JM, Chen MQ.
    Journal: Bioorg Med Chem Lett; 2005 Feb 01; 15(3):839-42. PubMed ID: 15664868.
    Abstract:
    The stereochemistry at C2'' and C3'' of two diastereomers of 2'',3''-dibromo-7-epi-10-deacetylcephalomannine (6 and 7), which were synthesized by reacting 7-epi-10-deacetylcephalomannine (5) with bromine, were assigned unambiguously based on crystallographic studies of 6. The X-ray crystallographic analysis shows that 6 adopts an absolute configuration of (2''S,3''R), and 7 can be assigned as (2''R,3''S) configuration. The side-chain conformation of 6 was revealed to be different with the known hydrophobic collapse and the apolar conformations, as found in solid state and in solution. However, most side-chain torsion angles of 6 were found to be very similar to those of tubulin-bound T-shaped conformation (T-Taxol). Both 6 and 7 showed strong in vitro paclitaxel-like activity.
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