Site-Selective Chemoenzymatic Glycosylation of an HIV-1 Polypeptide Antigen with Two Distinct N-Glycans via an Orthogonal Protecting Group Strategy.
Site-Selective Chemoenzymatic Glycosylation of an HIV-1 Polypeptide Antigen with Two Distinct N-Glycans via an Orthogonal Protecting Group Strategy.
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DOI：
10.1021/acs.joc.6b01044
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发表时间：
2016-08-05
期刊：
影响因子：
--
通讯作者：
Wang LX
中科院分区：
文献类型：
--
作者：
Toonstra C;Amin MN;Wang LX
描述了用于在多肽中顺序安装不同N-聚糖的会聚化学酶促方法。该方法包括在自动化固相肽合成（SPPS）过程中引入可保护的GlcNAc-Asn结构单元，然后对GlcNAc引物进行正交脱保护，并通过糖苷酶催化的转糖基化反应对糖链进行位点选择性顺序延伸。观察到一个相邻GlcNAc部分上的保护基对另一个GlcNAc受体在转糖基化中对一些内切糖苷酶的底物活性具有影响。该合成策略的有用性通过广泛HIV中和抗体PG 9的糖肽中和表位的有效合成来例证。该方法应普遍适用于合成携带多种不同N-聚糖的复合糖肽。
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.
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DOI：
10.1126/science.1213256
发表时间：
2011-11-25
期刊：
Science (New York, N.Y.)
影响因子：
--
作者：
Pejchal R;Doores KJ;Walker LM;Khayat R;Huang PS;Wang SK;Stanfield RL;Julien JP;Ramos A;Crispin M;Depetris R;Katpally U;Marozsan A;Cupo A;Maloveste S;Liu Y;McBride R;Ito Y;Sanders RW;Ogohara C;Paulson JC;Feizi T;Scanlan CN;Wong CH;Moore JP;Olson WC;Ward AB;Poignard P;Schief WR;Burton DR;Wilson IA
通讯作者：
Wilson IA
影响因子：
15
作者：
Amin, Mohammed N.;Huang, Wei;Mizanur, Rahman M.;Wang, Lai-Xi
通讯作者：
Wang, Lai-Xi
影响因子：
2.1
作者：
Holm, B;Linse, S;Kihlberg, J
通讯作者：
Kihlberg, J
影响因子：
15
作者：
Hackenberger, CPR;Friel, CT;Imperiali, B
通讯作者：
Imperiali, B
影响因子：
64.5
作者：
Garces F;Sok D;Kong L;McBride R;Kim HJ;Saye-Francisco KF;Julien JP;Hua Y;Cupo A;Moore JP;Paulson JC;Ward AB;Burton DR;Wilson IA
通讯作者：
Wilson IA