| 163228-28-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 163228-28-2
• 化学式: C₅₆H₇₇NO₃₄
• 分子量: 1308.21
• InChiKey: YSDPNGPNNMULEY-MJKIRTJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.04
• 重原子数：
  91.0
• 可旋转键数：
  24.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  427.77
• 氢给体数：
  1.0
• 氢受体数：
  34.0

反应信息

• 作为反应物：
  描述：

  在 DMDO 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
• 作为产物：
  描述：

  乙酸酐 、 在 吡啶 作用下， 生成
  参考文献：
  名称：

  Behar, Victor; Danishefsky, Samuel J., Angewandte Chemie, 1994, vol. 106, # 14, p. 1536 - 1538

  摘要：

  DOI：

文献信息

• Application of the Glycal Assembly Method to the Concise Synthesis of Neoglycoconjugates of Ley and Leb Blood Group Determinants and of H-Type I and H-Type II Oligosaccharides
  作者：Samuel J. Danishefsky、Victor Behar、John T. Randolph、Kenneth O. Lloyd

  DOI：10.1021/ja00126a011

  日期：1995.5

  The power of the glycal assembly strategy for reaching Lewis and H-type blood group determinants is demonstrated herein. Three key elements form the basis of the method. Thus, alpha-epoxides derived from galactal cyclic carbonate 13 are produced stereospecifically and are highly effective beta-galactosyl donors. Also, 6-monoprotected glucals can be regiospecifically glycosylated at the C-3 hydroxyl (see 23 + 13 --> 24). Moreover, glycosylation via a glycal epoxide produces a unique C-2 hydroxyl in the product which can be exploited as the acceptor site for branching (see formation of 26).
• Hydroxynorleucine as a glycosyl acceptor is an efficient means for introducing amino acid functionality into complex carbohydrates
  作者：Stacy J. Keding、Endo Atsushi、Kaustav Biswas、Andrzej Zatorski、Don M. Coltart、Samuel J. Danishefsky

  DOI：10.1016/s0040-4039(03)00517-3

  日期：2003.4

  A new approach to the synthesis of biologically relevant glycosyl amino acids using a non-natural amino acid as the glycosyl acceptor is described. The procedure involves a glycosylation reaction of a suitable carbohydrate donor with Fmoc-L-hydroxynorleucine benzyl ester. This reaction results in the direct incorporation of the amino acid moiety. The acceptor can be used for the preparation of alpha- or beta-O-linked glycosides depending upon the nature of the glycosyl donor. This method has been applied in the synthesis of six different tumor-associated carbohydrate antigens. (C) 2003 Elsevier Science Ltd. All rights reserved.