Syntheses of arsinolipids: non-isosteric analogues of phospholipids

Abstract

Reaction of alkaline benzenearsonous and 2,3‐dihydroxypropylarsonous acids with rac‐glycidol affords the corresponding arsinic acids, which after reduction with thiophenol are acylated with either fatty‐acid chlorides/pyridine or fatty acids/dicyclohexylcarbodiimide/4‐dimethylaminopyridine and oxidized with hydrogen peroxide to give the arsinolipids (rac‐2,3‐diacyloxypropyl)phenylarsinic and bis‐(rac‐2,3‐diacyloxypropyl)arsinic acids. The latter is a non‐isosteric analogue of bisphosphatidic acid. Copyright © 2000 John Wiley & Sons, Ltd.

Capability of arsonolipids to transport divalent cations: a Pressman cell study

“…2). Slight hydrolysis of the arsonolipids (2) cannot account for the shape of these curves because they are quite stable (Kordalis and Ioannou, 2000). Similar kinetics (initially linear with a tendency to reach a final saturation point) have previously been observed in amino acid transport experiments (Behr and Lehn, 1975).…”

Preparation of 2-Picolylarsonic Acid and its Reductive Cleavage by Ascorbic Acid/Iodine and by Thiophenol

“…Since triphenylphosphine oxide was detected by TLC, then the 2-picolylarsenoso compound must have been formed and it was detected by 1 H-NMR [(ArCH 2 AsO) x : 3.46 ppm compared to (PhCH 2 AsO) x : 3.50 ppm 16 ]. 3,4 More recently, the RAs(SR ) 2 was exploited as a precursor of the nucleophile RAsO 2− 2 for the construction of more complex arsinolipids. Thus, the main route that has been followed was the attack of a nucleophile (most probably the Ph 3 P) on the α-carbon of the intermediate 16 with the expulsion of H 2 AsO − 3 which was isolated as As 2 O 3 .…”

Σύνθεση Νέων Αρσονολιπιδίων (2,3,4-Τριακυλοξυβουτυλαρσονικών Οξέων)

“…Αλλα λιπίδια που περιέχουν αρσενικό [46], και τα οποία προκύπτουν κατά τη σύνθεση αρσινολιπιδίων 22 και 23 [47], και 25 [48]: • Η πορεία Α περιγράφεται στο κεφάλαιο 4.…”