Derivatized biotin compounds and methods of use

An efficient synthesis for the selective and efficient 1'-N derivatization of biotin is reported. The derivatized biotin acts as a stable analog of the carboxyphosphate intermediate in naturally-occurring biotin-mediated CO2 transfer. The synthesis may readily be scaled up to perform large-scal...

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Bibliographic Details
Main Authors STRONGIN ROBERT M, WALDROP GROVER L, SARAIVA MARCELO C, AMSPACHER DAVID R
Format Patent
LanguageEnglish
Published 29.04.2003
Edition7
Subjects
ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAININGELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN,SULFUR, SELENIUM OR TELLURIUM
CHEMISTRY
HETEROCYCLIC COMPOUNDS
HUMAN NECESSITIES
HYGIENE
MEDICAL OR VETERINARY SCIENCE
METALLURGY
ORGANIC CHEMISTRY
PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS ORMEDICINAL PREPARATIONS
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Summary:An efficient synthesis for the selective and efficient 1'-N derivatization of biotin is reported. The derivatized biotin acts as a stable analog of the carboxyphosphate intermediate in naturally-occurring biotin-mediated CO2 transfer. The synthesis may readily be scaled up to perform large-scale, selective acylations of biotin. The stable analog of the intermediate can inhibit the activity of the biotin carboxylase enzymes such as acetyl CoA carboxylase, and HIV protease. The functionalization at the 1'-N of biotin results in the attachment of an electrophilic "handle" amenable to reaction with a wide variety of nucleophiles to generate a new family of biotin analogs.
Bibliography:Application Number: US20010828359