S-(2-acetamido-2-deoxy-α-D-galactosyl)-N-(acetyl)-L-cysteine methylamide | 1533407-87-2

• 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-(2-acetamido-2-deoxy-α-D-galactosyl)-N-(acetyl)-L-cysteine methylamide
• 英文别名: Ac-L-Cys(α-D-GalNAc)-NHMe；(2R)-2-acetamido-3-[(2R,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]sulfanyl-N-methylpropanamide
• CAS: 1533407-87-2
• 化学式: C₁₄H₂₅N₃O₇S
• 分子量: 379.434
• InChiKey: ALMYIVYXGMRAJQ-NGBGQIEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  183
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  S-(tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactosyl)-N-Fmoc-L-cysteine 在 哌啶 、 吡啶 、 甲醇 、 sodium methylate 、 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 3.08h， 生成 S-(2-acetamido-2-deoxy-α-D-galactosyl)-N-(acetyl)-L-cysteine methylamide
  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

• <i>S</i>-Michael Additions to Chiral Dehydroalanines as an Entry to Glycosylated Cysteines and a Sulfa-Tn Antigen Mimic
  作者：Carlos Aydillo、Ismael Compañón、Alberto Avenoza、Jesús H. Busto、Francisco Corzana、Jesús M. Peregrina、María M. Zurbano

  DOI：10.1021/ja411522f

  日期：2014.1.15

  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.