Val-Gln-Lys-Asp(SH)-Val-Thr-Ser-OMe | 1417994-96-7

• 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: Val-Gln-Lys-Asp(SH)-Val-Thr-Ser-OMe
• 英文别名: H-Val-Gln-Lys-Asp(SH)-Val-Thr-Ser-OMe；(3S)-3-[[(2S)-6-amino-2-[[(2S)-5-amino-2-[[(2S)-2-amino-3-methylbutanoyl]amino]-5-oxopentanoyl]amino]hexanoyl]amino]-4-[[(2S)-1-[[(2S,3R)-3-hydroxy-1-[[(2S)-3-hydroxy-1-methoxy-1-oxopropan-2-yl]amino]-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-4-oxobutanethioic S-acid
• CAS: 1417994-96-7
• 化学式: C₃₃H₅₉N₉O₁₂S
• 分子量: 805.951
• InChiKey: QWAKDXIMULEUOM-RTRJKPGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  55
• 可旋转键数：
  27
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  355
• 氢给体数：
  12
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  Val-Gln-Lys-Asp(SH)-Val-Thr-Ser-OMe 、 N,N'-diacetylchitobiosamine 在 copper(II) acetate monohydrate 、 1-羟基苯并三唑 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以53%的产率得到Val-Gln-Lys-Asp-[GlcNAcβ-4GlcNAc]-Val-Thr-Ser-OMe
  参考文献：
  名称：

  Rapid Formation of N-Glycopeptides via Cu(II)-Promoted Glycosylative Ligation

  摘要：

  Herein Is described the chemoselective Cu(II)-HOBt promoted chemical ligation of glycosylamines and peptide thioacids to give N-glycosylated peptides. The method is distinguished from other chemical approaches to peptide N-glycosylation in that (1) it can be employed In the presence of unprotected N-terminal and Lys side chain amines; (2) it Is remarkably fast, going to completion in under 30 min; and (3) It produces glycopeptides without attendant aspartimide formation.

  DOI：

  10.1021/ol302961s
• 作为产物：
  描述：

  Boc-Val-Gln(Tr)-Lys(Boc)-Asp(STmb)-Val-Thr(^tBu)-Ser(^tBu)-OMe 在 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以57%的产率得到Val-Gln-Lys-Asp(SH)-Val-Thr-Ser-OMe
  参考文献：
  名称：

  Rapid Formation of N-Glycopeptides via Cu(II)-Promoted Glycosylative Ligation

  摘要：

  Herein Is described the chemoselective Cu(II)-HOBt promoted chemical ligation of glycosylamines and peptide thioacids to give N-glycosylated peptides. The method is distinguished from other chemical approaches to peptide N-glycosylation in that (1) it can be employed In the presence of unprotected N-terminal and Lys side chain amines; (2) it Is remarkably fast, going to completion in under 30 min; and (3) It produces glycopeptides without attendant aspartimide formation.

  DOI：

  10.1021/ol302961s

文献信息

• Rapid Formation of N-Glycopeptides <i>via</i> Cu(II)-Promoted Glycosylative Ligation
  作者：Ryan Joseph、Frank Brock Dyer、Philip Garner

  DOI：10.1021/ol302961s

  日期：2013.2.15

  Herein Is described the chemoselective Cu(II)-HOBt promoted chemical ligation of glycosylamines and peptide thioacids to give N-glycosylated peptides. The method is distinguished from other chemical approaches to peptide N-glycosylation in that (1) it can be employed In the presence of unprotected N-terminal and Lys side chain amines; (2) it Is remarkably fast, going to completion in under 30 min; and (3) It produces glycopeptides without attendant aspartimide formation.