Synthesis of 1,2-dioxetanes and intermediates therefor

• Main Authors: BRONSTEIN IRENA Y, EDWARDS BROOKS
• Format: Patent
• Language: English
• Published: 09.07.2002
• Edition: 7
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAININGELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN,SULFUR, SELENIUM OR TELLURIUM; ADHESIVES; APPARATUS THEREFOR; BEER; BIOCHEMISTRY; CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOIDCHEMISTRY; CHEMISTRY; COMPOSITIONS OR TEST PAPERS THEREFOR; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL ORENZYMOLOGICAL PROCESSES; DERIVATIVES THEREOF; DYES; ENZYMOLOGY; GENERAL METHODS OF ORGANIC CHEMISTRY; HETEROCYCLIC COMPOUNDS; INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIRCHEMICAL OR PHYSICAL PROPERTIES; MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FORELSEWHERE; MEASURING; MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEICACIDS OR MICROORGANISMS; METALLURGY; MICROBIOLOGY; MISCELLANEOUS APPLICATIONS OF MATERIALS; MISCELLANEOUS COMPOSITIONS; MUTATION OR GENETIC ENGINEERING; NATURAL RESINS; NUCLEIC ACIDS; NUCLEOSIDES; NUCLEOTIDES; ORGANIC CHEMISTRY; PAINTS; PERFORMING OPERATIONS; PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL; PHYSICS; POLISHES; PROCESSES OF PREPARING SUCH COMPOSITIONS; SPIRITS; SUGARS; TESTING; THEIR RELEVANT APPARATUS; TRANSPORTING; VINEGAR; WINE

Compounds having the formula:wherein T is a polycycloalkylidene group (e.g., adamant-2-ylidene); R is a C1-20 alkyl, aralkyl or cycloalkyl group; and Y is a fluorescent chromophore (e.g.,m-phenylene), produced by reacting a compound having the formula:with an R-ylating agent (e.g., R2 SO4) in the presence of an alkali metal alkoxide in a polar aprotic solvent. Also, compounds having the formula:are produced by reacting a compound having the formula:withwherein X is an electronegative leaving group (e.g., a halogen anion such as chloride ion) in the presence of a Lewis base (e.g., a trialkyl-amine) dissolved in an aprotic organic solvent (e.g., benzene or toluene). Also, compounds having the formulaare produced by reacting a compound of the formulawith a tetra-O-acylated-O-hexopyranoside halide, then hydrolyzing off the protective acyl groups. The aforementioned compounds and procedures are useful in the synthesis of enzyme-cleavable 1,2-dioxetane ring systems that can serve as members of a binding pair employed, for example, in chemiluminescent immunoassays, DNA probe assays, and direct assays for an enzyme.