126550-86-5Relevant articles and documents
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.
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
