126550-86-5Relevant academic research and scientific papers
A Diversity-Oriented Strategy for Chemoenzymatic Synthesis of Glycosphingolipids and Related Derivatives
Li, Qingjiang,Jaiswal, Mohit,Rohokale, Rajendra S.,Guo, Zhongwu
, p. 8245 - 8249 (2020/11/18)
A diversity-oriented strategy combining enzymatic glycan assembly and on-site lipid remodeling via chemoselective cross-metathesis and N-acylation was developed for glycosphingolipid (GSL) synthesis starting from a common, simple glycoside. The strategy was verified with a series of natural GSLs and GSL derivatives and showed several advantages. Most notably, it enabled two-way diversification of the glycan and lipid, including introduction of designed molecular tags, to provide functionalized GSLs useful for biological studies and applications.
A concise synthesis of globotriaosylsphingosine
Gold, Henrik,Boot, Rolf G.,Aerts, Johannes M.F.G.,Overkleeft, Herman S.,Codee, Jeroen D.C.,Van Der Marel, Gijs A.
scheme or table, p. 1652 - 1663 (2011/05/16)
Globotriaosylsphingosine (lysoCTH) is produced in the cell by deacylation of the globo-sphingolipid globotriaosylceramide. The latter compound is the major storage material encountered in Fabry patients, an inherited lysosomal storage disorder characteriz
Glycosynthase-mediated synthesis of glycosphingolipids
Vaughan, Mark D.,Johnson, Karl,DeFrees, Shawn,Tang, Xiaoping,Warren, R. Antony J.,Withers, Stephen G.
, p. 6300 - 6301 (2007/10/03)
Glycosphingolipids play crucial roles in virtually every stage of the cell cycle, and their clinical administration has been proposed as a treatment for Alzheimer's, Parkinson's, stroke, and a range of other conditions. However, lack of supply has severely hindered testing of this potential. A novel glycosynthase-based synthetic strategy is demonstrated, involving a mutant of an endoglycoceramidase in which the catalytic nucleophile has been ablated. This mutant efficiently couples a range of glycosyl fluoride donors with a range of sphingosine-based acceptors in yields around 95%. This technology opens the door to large-scale production of glycosphingolipids and, thus, to clinical testing. Copyright
Total synthesis of globotriaosylceramide (Gb3) and lysoglobotriaosylceramide (lysoGb3)
Nicolaou, Kyriacos C.,Caulfield, Thomas J.,Katoaka, Hideaki
, p. 177 - 191 (2007/10/02)
We have recently reported a highly efficient and stereocontrolled synthesis of globotriaosylceramide (Gb3, 1) in optically pure form.Key to our synthetic strategy was the implementation of the two-stage activation of thioglycosides for formatio
