S-(tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactosyl)-N-Fmoc-L-cysteine | 1533407-86-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: S-(tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactosyl)-N-Fmoc-L-cysteine
• 英文别名: Fmoc-L-Cys(α-(OAc)₃-D-GalNAc)-OH
• CAS: 1533407-86-1
• 化学式: C₃₂H₃₆N₂O₁₂S
• 分子量: 672.71
• InChiKey: RFSHVQJYBQLYPD-UKFUGAQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.37
• 重原子数：
  47.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  192.86
• 氢给体数：
  3.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  S-(tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactosyl)-N-Fmoc-L-cysteine 在 哌啶 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 0.58h， 生成 L-Cys(α-D-(OAc)3GalNAc)-NHMe
  参考文献：
  名称：

  S-Michael Additions to Chiral Dehydroalanines as an Entry to Glycosylated Cysteines and a Sulfa-Tn Antigen Mimic

  摘要：

  Stereoselective sulfa-Michael addition of appropriately protected thiocarbohydrates to chiral dehydroalanines has been developed as a key step in the synthesis of biologically important cysteine derivatives, such as S-(beta-D-glucopyranosyl)-D-cysteine, which has not been synthesized to date, and S-(2-acetamido-2-deoxy-alpha-D-galactopyranosyl)-L-cysteine, which could be considered as a mimic of Tn antigen. The corresponding diamide derivative was also synthesized and analyzed from a conformational viewpoint, and its bound state with a lectin was studied.

  DOI：

  10.1021/ja411522f
• 作为产物：
  描述：

  S-(2-acetamido-2-deoxy-α-D-galactosyl)-L-cysteine hydrochloride 在 吗啉 、 吡啶 、 四(三苯基膦)钯 、 碳酸氢钠 、 caesium carbonate 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 2.0h， 生成 S-(tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactosyl)-N-Fmoc-L-cysteine
  参考文献：
  名称：

  S-Michael Additions to Chiral Dehydroalanines as an Entry to Glycosylated Cysteines and a Sulfa-Tn Antigen Mimic

  摘要：

  Stereoselective sulfa-Michael addition of appropriately protected thiocarbohydrates to chiral dehydroalanines has been developed as a key step in the synthesis of biologically important cysteine derivatives, such as S-(beta-D-glucopyranosyl)-D-cysteine, which has not been synthesized to date, and S-(2-acetamido-2-deoxy-alpha-D-galactopyranosyl)-L-cysteine, which could be considered as a mimic of Tn antigen. The corresponding diamide derivative was also synthesized and analyzed from a conformational viewpoint, and its bound state with a lectin was studied.

  DOI：

  10.1021/ja411522f

文献信息

• IMMUNOGENIC VACCINE
  申请人：University of Georgia Research Foundation, Inc.

  公开号：US20150299290A1

  公开（公告）日：2015-10-22

  A glycolipopeptide comprising a carbohydrate component, a lipid component, and a MUC1 peptide component that induces both a humoral and a cellular immune response for use as a therapeutic or prophylactic vaccine.

  一种含有碳水化合物组分、脂质组分和MUC1肽组分的糖脂肽，可诱导细胞免疫和体液免疫反应，用作治疗或预防性疫苗。