Fluorescent labeling is an effective tool to quantify reagent activity and screen for affinity, reactivity and catalysis. It also provides a facile connection between the chemical synthesis and complex biological inquiries. Tuning substrate excitation and emission wavelengths within the right experimental framework can provide a powerful analytical methodology unmatched by other classes of molecular probe. Substrate choice is limited, however, by synthetic access to appropriate fluorescent tags. They must not only conform to optimal photophysical properties but offer minimum biomolecular interactivity within genomic, proteomic, metabolomic or systems-based biological experimentation.
Availability of the synthetic chemist’s set of standardized fluorophores now promises to simplify the life of Life Science researchers. The surroGATE family of labels exploits chemical activity that is modulated by a unique functional handle built onto one centralized core-dye framework. This family offers a robust blue dye based on dimethylaminocoumarin-4-acetamide (surroGATE-B). This dye has undergone extensive biological activity screening and provides minimal interference in proteomic, genomic or systems-wide biological studies. surroGATE-B dyes have been conjugated with vast array of natural products, proteins, oligonucleotides, and carbohydrates. surroGATE-B dyes are available as an array of chemical functionalities for rapid labeling of diverse-set of functional groups.
For example, the surroGATE-B2O, an alcohol terminated label, is useful in screening for oxidation conditions, including oxidation catalysts, and can be used to label chemical species through esterification, etherification or glycosylation chemistry. It is compatible with a variety of synthetic methods such as Mitsunobu esterification, as well as strategies employing Schmidt, Kahne, and glycal glycosylation methodologies.
SurroGATE labels can be rapidly attached to natural products and synthetic materials, and their localization within cells may be readily determined by fluorescence microscopy. The surroGATE label is compatible with a number of modern fluorescent methods including conventional fluorescence microscopy, LED fluorescence microscopy, two-photon microscopy, confocal microscopy, confocal fluorescence correlation spectroscopy (FCS), and single molecule spectroscopy, thereby providing a fundamental tool for converting chemical species into biophotonic probes. The example below illustrates the use of SURROGATE-B2A, an amine terminated label, to conjugate okadic acid and target the endoplasmic reticulum (ER). This image was collected on human tumor cell line (HeLa) using a confocal microscope.
The surroGATE family of labels is found together in the alphabetical section of our printed catalog as 7-dimethylaminocoumarin derivatives. We welcome your inquiries regarding the use of these and similar chemical resources.
surroGATE-B2O (7-dimethylaminocoumarin-4-acetamide) with 1° alcohol terminus useful in screening for oxidation conditions and catalysts. This material can be used to label chemical species through esterification, etherification or glycosylation chemistry. It is compatible with a variety of synthetic methods such as Mitsunobu esterification, as well as strategies employing the Schmidt, Kahne, and glycal glycosylation methodologies.
surroGATE-B2N (7-dimethylaminocoumarin-4-acetamide) having an ethylammonium trifluoroacetate terminus; acts as a hard nucleophile and is particularly useful for amide tagging. This label is compatible with methods such as imine formation and reductive amination.
surroGATE-B2S (7-dimethylaminocoumarin-4-acetamide) with primary thiol terminus; acts as a soft nucleophile useful in screening for oxidation conditions; this label is compatible with methods involving Michael additions and thioacetal formation.
surroGATE-B4A (7-dimethylaminocoumarin-4-acetamide) with a 1,1-dimethoxybutane terminus; useful for acetal tagging, and compatible with various aldol chemistries.
surroGATE-B2M (7-dimethylaminocoumarin-4-acetamide) terminated by an N-ethylmaleimide group; can function in the role of a Michael acceptor; this label is compatible with Diels-Alder reactions and many cycloaddition chemistries.
surroGATE-B1Y (7-dimethylaminocoumarin-4-acetamide) with a propargyl group (methylacetylene) acting as a functional handle; this label is compatible with chemistries of unsaturated molecules, including 1,2-additions and Huisgen [3+2] cycloadditions.
surroGATE-B1S (7-dimethylaminocoumarin-4-acetamide) featuring a terminal succinimide connected via an acetate function; also useful for amide tagging; this label is compatible with a variety of esterifications and glycosilylations.
surroGATE-B2E (7-dimethylaminocoumarin-4-acetamide) with a terminal double bond in the form of a butene group, useful in screening hydrogenations and olefin metatheses; this label is compatible with hydroborations as well as a variety of cycloaddition methods.
SURROGATE -B3Z (7-dimethylaminocoumarin-4-acetamide) with a terminal azide group attached with a three-carbon link; this label is compatible with Staudinger reactions, and also can be used with the Huisgen [3+2] cycloaddition method.
surroGATE-B2K (7-dimethylaminocoumarin-4-acetamide) having a 2-butanone terminus, useful in screening for reduction conditions; this label is compatible with Aldol chemistries as well as Staudinger reactions.
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