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    • 1. 发明授权
      US07524821B2 Scaffolded maleimide clusters for multivalent peptide assembly 有权
    • Scaffolded maleimide clusters for multivalent peptide assembly
    • US07524821B2
    • 2009-04-28
    • US10518108
    • 2003-06-20
    • Lai-Xi Wang , Jiahong Ni , Hengguang Li , Suddham Singh
    • Lai-Xi Wang , Jiahong Ni , Hengguang Li , Suddham Singh
    • A61K31/70 , A01N43/04
    • C07D207/452 , A61K38/00 , C07D207/456 , C07J41/0055 , C07J43/003 , C07K1/1077
    • Disclosed are scaffolded maleimide clusters, methods of making said clusters and use of said clusters as templates for multivalent peptide assembly. Multiple maleimide functionalities were introduced onto a scaffold molecule by the reaction of a core-centered polyamines with methoxycarbonylmaleimide or with activated esters of maleimide-containing compounds. The scaffolded maleimides allow rapid, highly chemoselective, and high-yield ligation with thiolcontaining peptides under virtually neutral conditions at room temperature. The disclosed mild and highly efficient ligation method is extremely valuable for synthesizing large and complex multivalent peptides that may not be easily obtained by conventional ligation methods. These novel scaffolded maleimide clusters allow a highly chemoselective ligation with a thiolcontaining peptide under virtually neutral conditions, providing a new and efficient approach for multivalent peptide assembly. The disclosed mild and highly efficient ligation method is extremely valuable for synthesizing large and complex multivalent peptides that may not be easily obtained by conventional ligation methods. A series of multivalent peptides containing the sequence of the 36-mer HIV-1 inhibitor DP178 (T20), the T-helper epitope from tetanus toxoid (830-844), and the minimum epitope sequence of the potent HIV-neutralizing antibody 2F5 were synthesized. Carbohydrates and cholic acid were chosen as the scaffold because of their rigidity and mufti-functionality. Thus, the topology of the multivalent peptides can be controlled by the defined spatial orientation of the maleimide functionalities on the rigid scaffold core. The resulting multivalent gp41 peptides incorporating strands of DP178 on the monosaccharide and the cholic acid templates were found to be able to form three or four a-helix bundles. Moreover, the multivalent peptides containing strands of the long gp41 peptide DP178 were highly immunogenic and were able to raise high titers of peptide-specific antibodies in the absence of any additional adjuvant. Therefore, these and related multivalent peptides constructed on the maleimide clusters may be used as novel immunogens, potential inhibitors, protein mimics, artificial proteins, and powerful antigens for a broad range of biomedical applications.
    • 基本信息 添加关注 加入工作空间 PDF全文 PDF下载 全文下载 相似专利 双屏查看 权利要求书 说明书全文 Espacenet 法律信息 同族专利 专利引用
    • 3. 发明申请
      US20050159341A1 Scaffolded maleimide clusters for multivalent peptide assembly 有权
    • Scaffolded maleimide clusters for multivalent peptide assembly
    • US20050159341A1
    • 2005-07-21
    • US10518108
    • 2003-06-20
    • Lai-Xi Wang , Jianghong Ni , Hengguang Li , Sudham Singh
    • Lai-Xi Wang , Jianghong Ni , Hengguang Li , Sudham Singh
    • A61K31/724 , A61K38/00 , A61K38/16 , C07D207/44 , C07D207/452 , C07D207/456 , C07D487/22 , C07J41/00 , C07J43/00 , C07K1/107 , C07K9/00 , C07D43/14
    • C07D207/452 , A61K38/00 , C07D207/456 , C07J41/0055 , C07J43/003 , C07K1/1077
    • Disclosed are scaffolded maleimide clusters, methods of making said clusters and use of said clusters as templates for multivalent peptide assembly. Multiple maleimide functionalities were introduced onto a scaffold molecule by the reaction of a core-centered polyamines with methoxycarbonylmaleimide or with activated esters of maleimide-containing compounds. The scaffolded maleimides allow rapid, highly chemoselective, and high-yield ligation with thiolcontaining peptides under virtually neutral conditions at room temperature. The disclosed mild and highly efficient ligation method is extremely valuable for synthesizing large and complex multivalent peptides that may not be easily obtained by conventional ligation methods. These novel scaffolded maleimide clusters allow a highly chemoselective ligation with a thiolcontaining peptide under virtually neutral conditions, providing a new and efficient approach for multivalent peptide assembly. The disclosed mild and highly efficient ligation method is extremely valuable for synthesizing large and complex multivalent peptides that may not be easily obtained by conventional ligation methods. A series of multivalent peptides containing the sequence of the 36-mer HIV-1 inhibitor DP178 (T20), the T-helper epitope from tetanus toxoid (830-844), and the minimum epitope sequence of the potent HIV-neutralizing antibody 2F5 were synthesized. Carbohydrates and cholic acid were chosen as the scaffold because of their rigidity and mufti-functionality. Thus, the topology of the multivalent peptides can be controlled by the defined spatial orientation of the maleimide functionalities on the rigid scaffold core. The resulting multivalent gp41 peptides incorporating strands of DP178 on the monosaccharide and the cholic acid templates were found to be able to form three or four a-helix bundles. Moreover, the multivalent peptides containing strands of the long gp41 peptide DP178 were highly immunogenic and were able to raise high titers of peptide-specific antibodies in the absence of any additional adjuvant. Therefore, these and related multivalent peptides constructed on the maleimide clusters may be used as novel immunogens, potential inhibitors, protein mimics, artificial proteins, and powerful antigens for a broad range of biomedical applications.
    • 基本信息 添加关注 加入工作空间 PDF全文 PDF下载 全文下载 相似专利 双屏查看 权利要求书 说明书全文 Global Dossier Espacenet 法律信息 同族专利 专利引用
    • 9. 发明申请
      US20110070607A1 GLYCOPROTEIN SYNTHESIS AND REMODELING BY ENZYMATIC TRANSGLYCOSYLATION 有权
    • GLYCOPROTEIN SYNTHESIS AND REMODELING BY ENZYMATIC TRANSGLYCOSYLATION
    • 糖蛋白合成和重组通过酶转移蛋白
    • US20110070607A1
    • 2011-03-24
    • US12898284
    • 2010-10-05
    • Lai-Xi Wang
    • Lai-Xi Wang
    • C12P21/00 , C07K16/00 , C12N9/82 , C12N9/72 , C12N9/48 , C12N9/64 , C12N9/76 , C12N9/08
    • C07K16/00 , C07K17/10 , C12P21/005
    • A chemoenzymatic method for the preparation of a homogeneous glycoprotein or glycopeptide, including (a) providing an acceptor selected from the group consisting of GlcNAc-protein and GlcNAc-peptide; and (b) reacting the acceptor with a donor substrate including an activated oligosaccharide moiety, in the presence of a catalyst comprising endoglycosidase (ENGase), to transfer the oligosaccharide moiety to the acceptor and yield the homogeneous glycoprotein or glycopeptide. The donor substrate includes, in a specific implementation, a synthetic oligosaccharide oxazoline. A related method of glycoprotein or glycopeptide remodeling with a predetermined natural N-glycan or a tailor-made oligosaccharide moiety, and a method of remodeling an antibody including a heterogeneous sugar chain, are also described. The disclosed methodology enables glycoprotein drugs to be modified for prolonged half-life in vivo, reduced immunogenicity, and enhanced in vivo activity, and for targeting and drug delivery.
    • 一种用于制备均质糖蛋白或糖肽的化学酶学方法，包括（a）提供选自GlcNAc-蛋白和GlcNAc-肽的受体; 和（b）在含有糖苷内切酶（ENGase）的催化剂存在下使受体与包含活性寡糖部分的供体底物反应，将寡糖部分转移到受体并产生均质糖蛋白或糖肽。 在具体实施方式中，供体底物包含合成寡糖恶唑啉。 还描述了与预定的天然N-聚糖或定制寡糖部分的糖蛋白或糖肽重塑的相关方法，以及重组包含异质糖链的抗体的方法。 所公开的方法使得糖蛋白药物能够在体内延长半衰期，免疫原性降低，体内活性增强，靶向和药物递送等方面进行修饰。
    • 基本信息 添加关注 加入工作空间 PDF全文 PDF下载 全文下载 相似专利 双屏查看 权利要求书 说明书全文 Global Dossier Espacenet 法律信息 同族专利 专利引用
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