| 252267-20-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 252267-20-2
• 化学式: C₅₈H₈₃NO₃₅S
• 分子量: 1386.35
• InChiKey: DMNKOQJGKRCIED-CAYIYHLESA-N

反应信息

• 作为反应物：
  描述：

  苯甲酰氯 、 生成 Fuc2Ac3Ac4Ac(a1-2)Gal3Ac4Ac6Ac(b1-4)[Fuc2Ac3Ac4Ac(a1-3)]GlcNAc6Ac(b1-3)[Bz(-2)]Gal4Ac6Ac(b)-SEt
  参考文献：
  名称：

  Design and Synthesis of Le^y-Bearing Glycopeptides that Mimic Cell Surface Le^y Mucin Glycoprotein Architecture

  摘要：

  Five Lewis(y)-based glycopeptide anti-cancer vaccine candidates have been designed and synthesized to target tumor-associated cell-surface glycoprotein antigens and to improve the immunizing performance in comparison to related vaccines. The peptide backbone consisted of two regions, a glycodomain AcNH-SSS-and a nonglycosylated sequence,-AVAV-. The resultant glycopeptide was conjugated, via an additional spacer, to the lipid carrier PamCysSer. In this series of totally synthetic molecular vaccine candidates, one or three of the sequentially arranged serine residues were glycosylated. Furthermore, the Le(y) tetrasaccharide determinant region was kept constant while the internal glycan core was systematically varied. Glycal assembly was used to prepare the glycosyl donors, and two strategies were applied to provide the serine-O-linked polysaccharide domains. In the first approach, a protected serine derivative was attached directly to the fully elaborated glycan. Following this course, both alpha- and beta-Ser derivatives were accessed. In the second route, a GalNAc-alpha-Ser was joined with a glycosyl donor to afford exclusively the desired a-serine-linked product. The glycopeptides were assembled using iterative solution phase peptide coupling. Following global deprotection, the lipid carrier was then coupled to the glycopeptide, resulting in the targeted constructs. The synthesis of these molecular vaccine candidates constitutes an important advance that should enable rationalization of carbohydrate-induced immune response as well as identification of optimal Le(y)-based anti-cancer vaccine leads.

  DOI：

  10.1021/ja0011820
• 作为产物：
  描述：

  在 三氟乙酸 作用下， 生成
  参考文献：
  名称：

  Design and Synthesis of Le^y-Bearing Glycopeptides that Mimic Cell Surface Le^y Mucin Glycoprotein Architecture

  摘要：

  Five Lewis(y)-based glycopeptide anti-cancer vaccine candidates have been designed and synthesized to target tumor-associated cell-surface glycoprotein antigens and to improve the immunizing performance in comparison to related vaccines. The peptide backbone consisted of two regions, a glycodomain AcNH-SSS-and a nonglycosylated sequence,-AVAV-. The resultant glycopeptide was conjugated, via an additional spacer, to the lipid carrier PamCysSer. In this series of totally synthetic molecular vaccine candidates, one or three of the sequentially arranged serine residues were glycosylated. Furthermore, the Le(y) tetrasaccharide determinant region was kept constant while the internal glycan core was systematically varied. Glycal assembly was used to prepare the glycosyl donors, and two strategies were applied to provide the serine-O-linked polysaccharide domains. In the first approach, a protected serine derivative was attached directly to the fully elaborated glycan. Following this course, both alpha- and beta-Ser derivatives were accessed. In the second route, a GalNAc-alpha-Ser was joined with a glycosyl donor to afford exclusively the desired a-serine-linked product. The glycopeptides were assembled using iterative solution phase peptide coupling. Following global deprotection, the lipid carrier was then coupled to the glycopeptide, resulting in the targeted constructs. The synthesis of these molecular vaccine candidates constitutes an important advance that should enable rationalization of carbohydrate-induced immune response as well as identification of optimal Le(y)-based anti-cancer vaccine leads.

  DOI：

  10.1021/ja0011820