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Investigation of protecting group for sialic acid carboxy moiety toward sialylglycopeptide synthesis by the TFA-labile protection strategy
Tetrahedron ( IF 2.1 ) Pub Date : 2021-08-24 , DOI: 10.1016/j.tet.2021.132423
Shun Ito 1 , Yuya Asahina 1 , Hironobu Hojo 1
Affiliation  

The sialylation using sialyl donor with 2,6-dimethylbenzyl (DMBn) ester at C-1 carboxy group rapidly proceeded with good α-selectivity to yield sialyl-N-acetylgalactosaminylated 9-fluorenylmethoxycarbonyl (Fmoc) serine unit. The unit was used for the solid-phase peptide synthesis (SPPS) of the sialyl glycopeptide. The DMBn group was removed during the final deprotection by the trifluoroacetic acid (TFA) treatment keeping the sialyl bond intact and the desired sialyl glycopeptide was successfully obtained. This protecting group strategy provided easier access to sialyl glycoamino acids for sialyl glycopeptides synthesis.



中文翻译:

唾液酸羧基部分保护基团对唾液酸糖肽合成的 TFA 不稳定保护策略的研究

使用唾液酸供体与 C-1 羧基上的 2,6-二甲基苄基 (DMBn) 酯的唾液酸化迅速进行,具有良好的 α-选择性,产生唾液酸-N-乙酰半乳糖胺化 9-芴基甲氧基羰基 (Fmoc) 丝氨酸单元。该装置用于唾液酸糖肽的固相肽合成 (SPPS)。DMBn 基团在最后的脱保护过程中被三氟乙酸 (TFA) 处理去除,保持唾液酸键完整,并成功获得所需的唾液酸糖肽。这种保护基团策略为唾液酸糖肽合成提供了更容易获得唾液酸糖氨基酸的途径。

更新日期:2021-09-12
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