((2S)-2-(2-((R)-2-(2-acetamidoacetamido)-3-(methylthio)propanamido)acetamido)-4-(methylsulfinyl)butanoyl)-L-alanine | 1058727-42-6

• 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: ((2S)-2-(2-((R)-2-(2-acetamidoacetamido)-3-(methylthio)propanamido)acetamido)-4-(methylsulfinyl)butanoyl)-L-alanine
• CAS: 1058727-42-6
• 化学式: C₁₈H₃₁N₅O₈S₂
• 分子量: 509.605
• InChiKey: FFOQGBCUMCXZCI-FGGFIJINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.07
• 重原子数：
  33.0
• 可旋转键数：
  15.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  199.87
• 氢给体数：
  6.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  ((2S)-2-(2-((R)-2-(2-acetamidoacetamido)-3-(methylthio)propanamido)acetamido)-4-(methylsulfinyl)butanoyl)-L-alanine 在 甲酸 、 溴化氰 、 盐酸胍 、 碘化铵 、 二甲基硫 、 三氟乙酸 作用下， 以 水 为溶剂， 反应 40.25h， 以73%的产率得到Ac-GSGMA-OH
  参考文献：
  名称：

  揭示糖肽合成的潜在连接位点。

  摘要：

  DOI：

  10.1002/anie.200801097
• 作为产物：
  描述：

  4-硝基苯磺酸甲酯 、 在 edetate disodium 、 胍 、 三羟甲基氨基甲烷 、 2-巯基乙醇 作用下， 以 水 、 乙腈 为溶剂， 反应 0.42h， 生成 ((2S)-2-(2-((R)-2-(2-acetamidoacetamido)-3-(methylthio)propanamido)acetamido)-4-(methylsulfinyl)butanoyl)-L-alanine
  参考文献：
  名称：

  揭示糖肽合成的潜在连接位点。

  摘要：

  DOI：

  10.1002/anie.200801097

文献信息

• Synthesis of an MUC1 Glycopeptide Dendrimer Based on β-Cyclodextrin by Click Chemistry
  作者：Yan-Mei Li、Pu-Guang Chen、Zhi-Hua Huang、Zhan-Yi Sun、Qian-Qian Li、Yong-Xiang Chen、Yu-Fen Zhao

  DOI：10.1055/s-0036-1590796

  日期：2017.9

  Glycopeptide dendrimers are attractive candidates for biomedical applications. Here, an efficient method for preparing multivalent MUC1 glycopeptide dendrimers based on β-cyclodextrin is described. By using copper(I) bromide and thioanisole as a catalyst system, precisely defined heptavalent conjugates were efficiently obtained. Using this heptavalent glycopeptide dendrimer, we observed multivalent

  糖肽树枝状聚合物是生物医学应用的有吸引力的候选者。在这里，描述了一种基于β-环糊精制备多价 MUC1 糖肽树枝状聚合物的有效方法。通过使用溴化铜 (I) 和苯硫醚作为催化剂体系，可以有效地获得精确定义的七价共轭物。使用这种七价糖肽树状聚合物，我们观察到抗体和表位相互作用中识别和关联过程中的多价效应，这可能具有生物医学应用。
• Synthesis and immunological evaluation of MUC1 glycopeptide conjugates bearing N-acetyl modified STn derivatives as anticancer vaccines
  作者：An Xiao、Xiu-Jing Zheng、Chengcheng Song、Yue Gui、Chang-Xin Huo、Xin-Shan Ye

  DOI：10.1039/c6ob01092j

  日期：——

  problem. To solve this problem, several STn derivatives with N-acetyl modifications were synthesized and incorporated into a 20-amino acid MUC1 tandem repeat sequence. The modified STn-MUC1 glycopeptides were further connected to a carrier protein keyhole limpet hemocyanin (KLH). The immunological effects of these synthetic vaccine conjugates were evaluated using the BALB/c mouse model. The results showed

  糖蛋白MUC1是抗肿瘤疫苗开发的有吸引力的靶标。但是，MUC1的免疫原性仍然很弱。为了解决该问题，合成了几种具有N-乙酰基修饰的STn衍生物，并将其掺入20个氨基酸的MUC1串联重复序列中。修饰的STn-MUC1糖肽进一步与载体蛋白匙孔戚血蓝蛋白（KLH）连接。使用BALB / c小鼠模型评估了这些合成疫苗偶联物的免疫学作用。结果表明，疫苗V2引起与天然STn-MUC1抗原交叉反应的抗体的更高滴度。此外，引起的抗血清与STn-MUC1抗原阳性的肿瘤细胞反应，表明碳水化合物抗原修饰策略可能具有克服天然MUC1糖肽弱免疫原性的潜力。
• Synthesis of homogeneous antifreeze glycopeptides via a ligation–desulfurisation strategy
  作者：James Garner、Katrina A. Jolliffe、Margaret M. Harding、Richard J. Payne

  DOI：10.1039/b918021d

  日期：——

  Homogeneous glycopeptide analogues of fish antifreeze glycoproteins of discrete oligomeric length have been synthesised using a native chemical ligation-desulfurisation strategy.

  使用天然化学连接-脱硫策略已合成了寡核苷酸长度不连续的鱼类抗冻糖蛋白的同质糖肽类似物。
• Nε-Modified lysine containing inhibitors for SIRT1 and SIRT2
  作者：Tero Huhtiniemi、Tiina Suuronen、Maija Lahtela-Kakkonen、Tanja Bruijn、Sanna Jääskeläinen、Antti Poso、Antero Salminen、Jukka Leppänen、Elina Jarho

  DOI：10.1016/j.bmc.2010.06.035

  日期：2010.8

  Sirtuins catalyze the NAD(+) dependent deacetylation of N-epsilon-acetyl lysine residues to nicotinamide, O '-acetyl- ADP-ribose (OAADPR) and N-epsilon-deacetylated lysine. Here, an easy-to-synthesize Ac-Ala-Lys-Ala sequence has been used as a probe for the screening of novel N-epsilon-modified lysine containing inhibitors against SIRT1 and SIRT2. N-epsilon-Selenoacetyl and N-epsilon-isothiovaleryl were the most potent moieties found in this study, comparable to the widely studied N-epsilon-thioacetyl group. The N-epsilon-3,3-dimethylacryl and N-epsilon-isovaleryl moieties gave significant inhibition in comparison to the N-epsilon-acetyl group present in the substrates. In addition, the studied N-epsilon-alkanoyl, N-epsilon-alpha,beta-unsaturated carbonyl and N-epsilon-aroyl moieties showed that the acetyl binding pocket can accept rather large groups, but is sensitive to even small changes in electronic and steric properties of the N-epsilon-modification. These results are applicable for further screening of Ne-acetyl analogues. (C) 2010 Elsevier Ltd. All rights reserved.
• Aza-β3-amino acid containing peptidomimetics as cAMP-dependent protein kinase substrates
  作者：Ksenija Kisseljova、Aleksei Kuznetsov、Michèle Baudy-Floc’h、Jaak Järv

  DOI：10.1016/j.bioorg.2010.05.004

  日期：2010.10

  Peptidomimetic analogs of the peptide RRASVA, known as the "minimal substrate" of the catalytic subunit of the cAMP-dependent protein kinase (PKA), were synthesized by consecutive replacement of natural amino acids by their aza-beta(3) analogs. The peptidomimetics were tested as PKA substrates and the kinetic parameters of the phosphorylation reaction were determined. It was found that the interaction of these peptidomimetics with the enzyme active center was sensitive to the location of the backbone modification, while the maximal rate of the reaction was practically not affected by the structure of substrates. The pattern of molecular recognition of peptidomimetics was in agreement with the results of structure modeling and also with the results of computational docking study of peptide and peptidomimetic substrates with the active center of PKA. It was concluded that the specificity determining factors which govern substrate recognition by the enzyme should be grouped along the phosphorylatable substrate, and such clustering might open new perspectives for pharmacophore design of peptides and peptide-like ligands. (C) 2010 Elsevier Inc. All rights reserved.