Debabrata Bhattasali

Ketose-phosphonates may adopt open chain, or a- or b-furanosyl, or a- or b-pyranosyl configurational
isomers in aqueous solution. An HPLC and NMR analysis of a series of ketose-phosphonates with a thymidylyltransferase (dTDP-glucose pyrophosphorylase) implied a rapid dynamic equilibrium between the pyranosyl forms of gluco-ketose phosphonate leading to efficient production of unique
sugar nucleotide analogues. The preparation of diastereomerically pure gluco-configured monofluoromethylenephosphonates enabled the determination of the thymidylyltransferase preference for CHF stereochemistry. The effects of acidity upon thymidylyltransferase substrate specificity were determined using a series of monofluoro- and difluoro- ketose-phosphonates. WaterLOGSY NMR
spectroscopy demonstrated a switching of the ordered Bi-Bi mechanism with ketose-phosphonate substrates. Ketose-phosphonates are presented as a unique class of sugar 1-phosphate analogues with potential applications as glycosyltransferase probes

Schulzeines B (2) and C (3) were synthesized by a
convergent strategy using epimeric tricyclic lactam building
blocks, 4 and 5, and the C28 fatty acid side chain 6.
Syntheses of tricyclic lactams (4/5) were achieved by
Bischler-Napieralski reaction. Sharpless asymmetric dihydroxylation and BINAL-H-mediated asymmetric reduction
of an enone was employed to prepare the key fatty acid side
chain 6. The spectral as well as analytical data of 2 and 3
were in good agreement with the reported data for the natural
products, thus confirming their assigned structures.

ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.