Site-Selective Chemoenzymatic Glycosylation of an HIV-1 Polypeptide Antigen with Two Distinct N-Glycans via an Orthogonal Protecting Group Strategy,The Journal of Organic Chemistry

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Site-Selective Chemoenzymatic Glycosylation of an HIV-1 Polypeptide Antigen with Two Distinct N-Glycans via an Orthogonal Protecting Group Strategy
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2016-07-07 00:00:00 , DOI: 10.1021/acs.joc.6b01044
Christian Toonstra ₁ , Mohammed N. Amin ₁ , Lai-Xi Wang ₁

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A convergent chemoenzymatic approach for sequential installation of different N-glycans in a polypeptide is described. The method includes introduction of distinguishably protected GlcNAc-Asn building blocks during automated solid phase peptide synthesis (SPPS), followed by orthogonal deprotection of the GlcNAc primers and site-selective sequential extension of the sugar chains through glycosynthase-catalyzed transglycosylation reactions. It was observed that the protecting groups on one neighboring GlcNAc moiety have an impact on the substrate activity of another GlcNAc acceptor toward some endoglycosynthases in transglycosylation. The usefulness of this synthetic strategy was exemplified by an efficient synthesis of the glycopeptide neutralizing epitope of broadly HIV-neutralizing antibody PG9. The method should be generally applicable for the synthesis of complex glycopeptides carrying multiple different N-glycans.

中文翻译：

通过正交保护基团策略，具有两个不同的N-聚糖的HIV-1多肽抗原的位点选择性化学酶糖基化。

描述了用于在多肽中顺序安装不同N-聚糖的会聚化学酶法。该方法包括在自动固相肽合成（SPPS）期间引入区别保护的GlcNAc-Asn构建基块，然后通过糖合酶催化的转糖基化反应对GlcNAc引物进行正交脱保护，并进行糖链的位点选择性顺序延伸。观察到一个相邻的GlcNAc部分上的保护基在转糖基化中对另一种GlcNAc受体对某些内切糖合酶的底物活性有影响。有效合成广泛中和HIV的抗体PG9的糖肽中和表位证明了这种合成策略的实用性。

更新日期：2016-07-07

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