2,6,7-trithiabicyclo[2.2.2]octanes as promising photolabile tags for combinatorial encoding.
نویسندگان
چکیده
The adducts of trithiabicyclo[2.2.2]octane (TTBO) and carbonyl compounds undergo efficient photoinduced fragmentation with quantum yields comparable to that of dithiane adducts. The effect of the third sulfur on the stability of the respective radical cations and radicals is examined computationally and experimentally in a laser flash photolysis study. A straightforward synthetic approach to a variety of 4-substituted trithiabicyclo[2.2.2]octanes from 3-bromo-2,2-bis(bromomethyl)propanol is developed, making a diverse set of mass-differentiated photolabile tags readily available for combinatorial encoding.
منابع مشابه
Direct screening of solution phase combinatorial libraries encoded with externally sensitized photolabile tags.
Solution phase combinatorial chemistry holds an enormous promise for modern drug discovery. Much needed are direct methods to assay such libraries for binding of biological targets. An approach to encoding and screening of solution phase libraries has been developed based on the conditional photorelease of externally sensitized photolabile tags. The encoding tags are released into solution only...
متن کاملUnexpectedly similar charge transfer rates through benzo-annulated bicyclo[2.2.2]octanes.
A 4-(pyrrolidin-1-yl)phenyl electron donor and 10-cyanoanthracen-9-yl electron acceptor are attached via alkyne linkages to the bridgehead carbon atoms of bicyclo[2.2.2]octane and all three benzo-annulated bicyclo[2.2.2]octanes. The sigma-system of bicyclo[2.2.2]octane provides a scaffold having nearly constant bridge geometry on which to append multiple, weakly interacting benzo pi-bridges, so...
متن کاملCrystal structure of 4-methyl-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane
The title mol-ecule, C5H9O3P, has a bi-cyclo-[2.2.2] structure with the P atom at the prow and the bridge-head C atom, with the bonded methyl group, at the stern. The three six-membered rings in the bi-cyclo-[2.2.2] structure have essentially identical good boat conformations.
متن کاملPhotoactive Spatial Proximity Probes for Binding Pairs with Epigenetic Marks.
A new strategy for encoding polypeptide libraries with photolabile tags is developed. The photoassisted assay, based on conditional release of encoding tags only from bound pairs, can differentiate between peptides which have minor differences in a form of post-translational modifications with epigenetic marks. The encoding strategy is fully compatible with automated peptide synthesis. The enco...
متن کامل(1-Oxo-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octan-4-yl)methyl 4-methylbenzenesulfonate
In the title compound, C(12)H(15)O(7)PS, the P atom has a distorted tetra-hedral environment. The P-O-C-C torsion angles deviate significantly from zero [average = 12.0 (3)°], indicating that the bicyclic OP(OCH(2))(3)C cage is strained. In the crystal, weak C-H⋯O inter-actions consolidate the packing.
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
- The Journal of organic chemistry
دوره 73 1 شماره
صفحات -
تاریخ انتشار 2008