New safety-catch photolabile protecting group.
نویسندگان
چکیده
Photolabile protecting groups have proven their usefulness on many occasions. Their versions as linkers are however less attractive, as robustness and real orthogonality become critical issues. Safety-catch systems, where a preliminary activation phase is necessary, circumvent the problem of premature cleavage. In this work, we introduce a new safety-catch photolabile protecting group, whose cleavage requires the simultaneous presence of light and a chemical promoter.
منابع مشابه
Light-directed radial combinatorial chemistry: orthogonal safety-catch protecting groups for the synthesis of small molecule microarrays.
We describe the development of photolabile protecting groups based on the 3,4,5-trimethoxyphenacyl group (TMP). Orthogonal safety-catches were created by introducing an acid-activatible dimethyl ketal (AA-TMP) and an oxidatively activatible 1,3-dithiane (OA-TMP) into the photolabile TMP group. We demonstrate the application of these protecting groups in light-directed synthesis of small molecul...
متن کاملIntramolecular sensitization of photocleavage of the photolabile 2-(2-nitrophenyl)propoxycarbonyl (NPPOC) protecting group: photoproducts and photokinetics of the release of nucleosides.
Novel photolabile protecting groups based on the 2-(2-nitrophenyl)propoxycarbonyl (NPPOC) group with a covalently linked thioxanthone as an intramolecular triplet sensitizer exhibit significantly enhanced light sensitivity under continuous illumination. Herein we present a detailed study of the photokinetics and photoproducts of nucleosides caged with these new protecting groups. Relative to th...
متن کاملSynthesis of Fluorous Photolabile Aldehyde and Carbamate and Alkyl Carbamate Protecting Groups for Carbohydrate-Associated Amines
Two new fluorous photolabile-protecting groups (FNBC and FNB) and a new base-labile protecting group (FOC) for the masking of amines are reported. The protecting groups survive a wide range of common reaction conditions used in oligosaccharide synthesis and render the attached molecules amenable to fluorous solid-phase extraction (FSPE). A glycosyl acceptor containing the FNB group is shown to ...
متن کاملApplication of new photolabile protecting groups as photocleavable joints of block copolymers.
New photoresponsive block copolymers (BCPs) have been developed by incorporating photocleavable units. These photocleavable units are derived from robust photolabile protecting groups (PPGs); UV irradiation cleaves the BCPs and releases a well-defined chemically active functional group at the cleaved end of a PS polymer.
متن کاملo-nitrobenzyl photolabile protecting groups with red-shifted absorption: syntheses and uncaging cross-sections for one- and two-photon excitation.
We evaluated the o-nitrobenzyl platform for designing photolabile protecting groups with red-shifted absorption that could be photolyzed upon one- and two-photon excitation. Several synthetic pathways to build different conjugated o-nitrobenzyl backbones, as well as to vary the benzylic position, are reported. Relative to the reference 4,5-dimethoxy-2-nitrobenzyl group, several o-nitrobenzyl de...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Organic letters
دوره 9 26 شماره
صفحات -
تاریخ انتشار 2007