180187-58-0Relevant articles and documents
The use of 2-O-propagyloxycarbonyl protecting group in the selective formation of 1,2-trans-glycosidic linkage
Sato, Ken-ichi,Sakai, Koudai,Kojima, Masaru,Akai, Shoji
, p. 4423 - 4425 (2007)
The effect of N-phenylcarbamoyl (Car) and propagyloxycarbonyl (Poc) protecting groups at the O-2 position of donors was examined. The usefulness of Poc group in the selective formation of 1,2-trans-glycosidic linkage is shown by comparing the reactivity o
Picoloyl protecting group in synthesis: Focus on a highly chemoselective catalytic removal
Bandara, Mithila D.,Demchenko, Alexei V.,Geringer, Scott A.,Mannino, Michael P.
, p. 4863 - 4871 (2020/07/13)
The picoloyl ester (Pico) has proven to be a versatile protecting group in carbohydrate chemistry. It can be used for the purpose of stereocontrolling glycosylations via an H-bond-mediated Aglycone Delivery (HAD) method. It can also be used as a temporary protecting group that can be efficiently introduced and chemoselectively cleaved in the presence of practically all other common protecting groups used in synthesis. Herein, we will describe a new method for rapid, catalytic, and highly chemoselective removal of the picoloyl group using inexpensive copper(ii) or iron(iii) salts. This journal is
Contribution of phosphates and adenine to the potency of adenophostins at the IP3 receptor: Synthesis of all possible bisphosphates of adenophostin A
Sureshan, Kana M.,Riley, Andrew M.,Thomas, Mark P.,Tovey, Stephen C.,Taylor, Colin W.,Potter, Barry V. L.
, p. 1706 - 1720 (2012/05/04)
Although adenophostin A (AdA), the most potent agonist of d-myo-inositol 1,4,5-trisphosphate receptors (IP3R), is thought to mimic IP 3, the relative roles of the different phosphate groups and the adenosine motif have not been established. We synthesized all three possible bisphosphate analogues of AdA and glucose 3,4-bisphosphate (7, AdA lacking the 2′-AMP). 2′-Dephospho-AdA (6) was prepared via a novel regioselective dephosphorylation strategy. Assessment of the abilities of these bisphosphates to stimulate intracellular Ca2+ release using recombinant rat type 1 IP3R (IP3R1) revealed that 6, a mimic of Ins(4,5)P2, is only 4-fold less potent than IP3, while 7 is some 400-fold weaker and even 3′3-dephospho-AdA (5) is measurably active, despite missing one of the vicinal bisphosphate groups normally thought to be crucial for IP3-like activity. Compound 6 is the most potent bisphosphate yet discovered with activity at IP3R. Thus, adenosine has a direct role independent of the 2′-phosphate group in contributing toward the potency of adenophostins, the vicinal bisphosphate motif is not essential for activity at the IP3R, as always thought, and it is possible to design potent agonists with just two of the three phosphates. A model with a possible adenine-R504 interaction supports the activity of 5 and 6 and also allows a reappraisal of the unexpected activity previously reported for the AdA regioisomer 2′3-phospho-3′3- dephospho-AdA 40.
