Notiz über 2‐Alkoxymethyl‐Δ²‐thiazoline

A Selenium Analogue of Firefly D‐Luciferin with Red‐Shifted Bioluminescence Emission

“…[7] Furthermore, it is known that several enzymes recognize selenium analogues equally as well as the natural sulfur-containing substrates, [8] which makes it likely that the derivative would be an efficient luciferase substrate. Finally, on account of the red shift induced by the 6'-amino substituent in 3 b, and the usefulness of the amino group in the preparation of bioluminogenic substrates, [2d, 9] we chose to preserve this functionality in our design.The synthesis of native d-luciferin (3 a) [10b-d] and its analogue 6'-amino-d-luciferin (3 b) [6b] is straightforward and involves a condensation reaction [10] between 2-cyanobenzothiazole derivative 1 a,b and cysteine (2 a) (Scheme 1). Compound 3 b is a competent substrate for FLuc and exhibits redshifted BL emission with l em,max = 578 nm.…”

“…The synthesis of native d-luciferin (3 a) [10b-d] and its analogue 6'-amino-d-luciferin (3 b) [6b] is straightforward and involves a condensation reaction [10] between 2-cyanobenzothiazole derivative 1 a,b and cysteine (2 a) (Scheme 1). Compound 3 b is a competent substrate for FLuc and exhibits redshifted BL emission with l em,max = 578 nm.…”

Naturally occurring linear fused thiazoline-thiazole containing metabolites: total synthesis of (–)-didehydromirabazole A, a cytotoxic alkaloid from blue–green algae

“…The aqueous layer was separated and extracted with ether (3 x 20 cm3), and the combined ether extracts were dried and evaporated under reduced pressure to leave an oil. This was purified by chromatography on silica gel using 20% ethyl acetate-light petroleum as eluent to give the title compound (410 mg, 54%) as a colourless oil (1 : 1 mixture of diastereoisomers); Amax ( EtOH) (20), 326 (18), 325 (20), 324 (100) and 255 (55). The resulting solution was heated under reflux for 48 h and then washed with aqueous NaHCO, (30 an3).…”

A New Synthetic Methodology for Tiazofurin

“…Our strategy was to form thiazoline intermediate 6 by the cyclocondensation of cysteine ethyl ester hydrochloride ( 5 ) with nitrile 4 , which on dehydrogenation, followed by removal of the protecting groups, should provide the desired nucleoside 1 . Accordingly (see Scheme ), 1-cyano-2,3,5-tri- O -benzoyl- β - d -ribofuranose ( 4 ) 16 was allowed to react with cysteine ethyl ester hydrochloride in the presence of triethylamine at room temperature.…”