A Diversity-Oriented Strategy for Chemoenzymatic Synthesis of Glycosphingolipids and Related Derivatives

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.

开发了一种面向多样性的策略，该策略通过化学选择性交叉复分解和N -酰化结合酶促聚糖组装和原位脂质重塑，用于从一种常见的简单糖苷开始合成鞘糖脂（GSL）。该策略通过一系列天然鞘糖脂和鞘糖脂衍生物得到了验证，并显示出若干优势。最显著的是，它使聚糖和脂质能够双向多样化，包括引入设计的分子标签，从而提供可用于生物学研究和应用的功能化鞘糖脂。