Fmoc-Asn(GlcNAc)2-OH | 131368-10-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Fmoc-Asn(GlcNAc)2-OH
• 英文别名: (2S)-4-[[(2R,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-oxobutanoic acid
• CAS: 131368-10-0
• 化学式: C₃₅H₄₄N₄O₁₅
• 分子量: 760.752
• InChiKey: QQBVHSXSTHSIDG-GXTCOASPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  54
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  292
• 氢给体数：
  10
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  Fmoc-Asn(GlcNAc)2-OH 生成 (2S)-N'-[(2R,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]-2-[[(2S)-2-[[(2S,3S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[(2S)-6-amino-2-[(2-aminoacetyl)amino]hexanoyl]amino]propanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-hydroxybutanoyl]amino]-3-methylpentanoyl]amino]-3-phenylpropanoyl]amino]-N-[(2S)-6-amino-1-[[(2S,3R)-1-[[(2S)-1-[[(2S)-1-amino-4-methylsulfanyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxobutan-2-yl]amino]-1-oxohexan-2-yl]butanediamide
  参考文献：
  名称：

  OTVOS, LASZLO;URGE, LASZLO;HOLLOSI, MIKLOS;WROBLEWSKI, KRZYSZTOF;GRACZYK,+, TETRAHEDRON LETT., 31,(1990) N1, C. 5889-5892

  摘要：

  DOI：
• 作为产物：
  描述：

  N,N'-Diacetylchitobiose 在 碳酸氢铵 、 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 苯甲醚 、 三氟乙酸 作用下， 以 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 20.0~40.0 ℃ 、1.72 MPa 条件下， 反应 29.5h， 生成 Fmoc-Asn(GlcNAc)2-OH
  参考文献：
  名称：

  一种有效的合成途径，可用于糖肽合成的糖氨基酸结构单元。

  摘要：

  [反应：见正文]化学糖肽合成需要获得克量的糖基化氨基酸构件。因此，这种结构单元的合成效率非常重要。在这里，我们报告了一种快速高效的合成路线，可分三步以高收率从未保护的糖中合成Fmoc保护的天冬酰胺基糖苷。通过标准的Fmoc固相肽合成，将糖基化的氨基酸成功地掺入靶糖肽7和8中。

  DOI：

  10.1021/ol048342n

文献信息

• Spore-Encapsulating Glycosyltransferase Catalysis Tandem Reactions: Facile Chemoenzymatic Synthesis of Complex Human Glycans
  作者：Qiang Chao、Tianlu Li、Ji-Xiang Jia、Zijie Li、Peng Peng、Xiao-Dong Gao、Ning Wang

  DOI：10.1021/acscatal.1c05630

  日期：2022.3.4

  encapsulated on the surface of yeast spores, which enabled facile assembly of diverse naturally occurring sialyl-galactosylated glycans, including human milk oligosaccharide, N-glycan biomarker, O-Man glycan, and O-GalNAc glycan. The utility of this strategy was further demonstrated by systematic construction of a panel of Core 2 O-GalNAc glycans.

  唾液酸半乳糖 (Sia-Gal) 是寡糖最丰富的末端基序之一，广泛存在于动物的糖缀合物和未缀合聚糖中。为了研究它们的功能和生物学作用，必须获得末端结构确定的寡糖。在此，我们描述了一种使用固定化酶对具有末端半乳糖 (Gal) 或 Sia-Gal 残基的聚糖进行区域选择性修饰的便捷有效策略。半乳糖基转移酶 (GalT) 和唾液酸转移酶 (ST) 被包裹在酵母孢子的表面，这使得多种天然存在的唾液酸-半乳糖基化聚糖（包括人乳寡糖、N-聚糖生物标志物、O -Man聚糖和O-GalNAc聚糖。通过系统构建一组核心 2 O -GalNAc 聚糖进一步证明了该策略的实用性。
• Luminescence detection of peptide:<i>N</i>-glycanase activity using engineered split inteins
  作者：Tsuyoshi Takahashi、Tatsuya Uchibayashi、Nozomi Ishii、Ichiro Matsuo、Yukiko Yoshida、Tadashi Suzuki

  DOI：10.1039/d2cc04865e

  日期：——

  A convenient method to detect peptide:N-glycanase activity was developed using engineered split inteins in which the N-intein sequences contain N,N′-diacetylchitobiose.

  一种便利的方法来检测肽：使用工程分裂肽内切酶，其中N-肽内切酶序列包含N，N'-二乙酰壳聚糖。
• Solid-phase synthesis of glycopeptides: synthesis of Nα-Flourenylmethoxycarbonyl L-asparagine Nβ-glycosides
  作者：Laszlo Urge、Emma Kollat、Miklos Hollosi、Ilona Laczko、Krzysztof Wroblewski、Jan Thurin、Laszlo Otvos

  DOI：10.1016/0040-4039(91)80802-d

  日期：1991.7

  It was found that crude 1-glycosylamines, prepared with saturated aqueous NH4HCO3 from reducing sugars, can be coupled with Fmoc-Asp(OPfp)-O(t)Bu in N,N-dimethylformamide-water mixtures. Purification and removal of the (t)Bu group results in N-beta-glycosides of Fmoc-Asn-OH which can be used for the solid phase synthesis of glycopeptides.
• Glycopeptide probes for understanding peptide specificity of the folding sensor enzyme UGGT
  作者：Takaya Kudo、Makoto Hirano、Toshihiro Ishihara、Shun Shimura、Kiichiro Totani

  DOI：10.1016/j.bmcl.2014.11.013

  日期：2014.12

  A systematic series of chitobiose-modified pentapeptides with sequence variations of hydrophobic leucine and hydrophilic serine were synthesized. The resulting glycopeptides were used as molecular probes to elucidate aglycon peptide specificity of the glycoprotein-folding sensor enzyme UGGT. Inhibitory experiments with a synthetic fluorescent glyco-substrate and the glycopeptides revealed that UGGT prefers a serine residue directly linked to C-terminal of the N-glycosylation site in its substrate recognition. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis of N-linked glycopeptides on solid support and their evaluation as protease substrates
  作者：Mallesham Bejugam、Beatrice A. Maltman、Sabine L. Flitsch

  DOI：10.1016/j.tetasy.2004.11.031

  日期：2005.1

  A range of glycopeptides containing protease cleavage sites were synthesized on solid support using, Fmoc-based solid phase glycopeptide synthesis. The immobilized peptides were studied as substrates for the proteases chymotrypsin and thermolysin. For chymotrypsin, N-glycosylation of an Asn residue at the P-2 site appears to reduce hydrolysis whereas glycosylation of the P-2, site does not appear to affect peptide hydrolysis by thermolysin. (C) 2004 Elsevier Ltd. All rights reserved.