Synthesis and immunomodulating tumor control properties of albumin covalently connected to trehalose

Abstract

Summary. Proteins conjugated to a trehalose derivative are described. These include human serum albumin and bovine serum albumin covalently attached through appropriate molecular linkages to the 6-and 6,6'-positions of trehalose. The immunomodulating tumor control activities of these conjugated proteins has been assayed in several test systems.

Synthesis of Maradolipid

“…Any route starting with commercially available α,α-trehalose 2 would essentially entail a differentiation of two primary alcohols as a key step. Regioselective protection of trehalose polyol has been the subject of intense research. − Synthesis of TDM analogues received immense attention, and procedures affording diesters − or monoesters − have been developed, both by nucleophilic displacement of 6,6′-dideoxy derivatives bearing sulfonates ,,, or halides at 6,6′positions and by acylations of 6,6′-diol of trehalose, − , with its secondary hydroxyl groups protected as TMS − or benzyl − groups. Direct diacylations of unprotected trehalose using transesterification, Mitsunobu conditions, , and tributylstannylation are also reported.…”

“…In recent years, the trimethylsilyl group (TMS) has gained importance in carbohydrate synthesis, as evidenced by increasing number of publications involving this protection. − ,− Hindsgaul first explored the use of TMS ethers in glycosylation reaction. , The unique reactivity of TMS protecting group is further endorsed by two seminal studies, Hung’s TMSOTf catalyzed one-pot protection of carbohydrate polyols − and Gervay-Hague’s glycosyl iodide mediated one-pot stereoselective glycosylation protocols, − both involving per- O -silylated monosaccharides. Along with this, subsequent studies by Beau and co-workers first employing cat.…”

“…TMS groups are easy to introduce; they improve the solubility of parent sugar in organic solvents and are fairly stable. More importantly, the primary TMS ethers could be hydrolyzed − ,− or acetylated selectively in the presence of secondary TMS ethers. Finally, global deprotection could be achieved instantly and cleanly under mild conditions without disturbing the double bonds.…”