Department of Chemistry, University of Florida , 214 Leigh Hall, Gainesville, Florida 32611, United States.
Org Lett. 2017 Jun 16;19(12):3063-3066. doi: 10.1021/acs.orglett.7b01132. Epub 2017 May 25.
A new strategy has been developed for GPI glycan-peptide conjugate synthesis based upon a traceless Staudinger reaction between a peptide phosphinothioester and a GPI glycan azide. The strategy was first studied and optimized with simple peptides and GPI glycans, which offered excellent yields of the desired conjugates in both organic and aqueous solvents. It was then used to successfully synthesize an analogue of the human CD52 antigen containing the whole CD52 peptide sequence and the conserved trimannose motif of all GPI anchors.
一种新的 GPI 糖肽缀合物合成策略是基于肽膦硫酯与 GPI 糖基叠氮化物之间的无痕 Staudinger 反应开发的。该策略首先使用简单的肽和 GPI 糖进行了研究和优化,在有机和水溶剂中均能以优异的收率得到所需的缀合物。然后,该策略成功地合成了一种含有完整 CD52 肽序列和所有 GPI 锚定保守三甘露糖基序的人 CD52 抗原类似物。