sungsanpin | 1435677-74-9

• 分子结构分类: 有机化合物 - 有机聚合物 - 多肽
• 英文名称: sungsanpin
• 英文别名: Sungsanpin；(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-2-[[(3S,6S,12S,19S,22S,25S)-3-(4-aminobutyl)-12-benzyl-22-[(2S)-butan-2-yl]-6-(hydroxymethyl)-2,5,8,11,14,17,21,24-octaoxo-1,4,7,10,13,16,20,23-octazabicyclo[23.3.0]octacosane-19-carbonyl]amino]-3-hydroxypropanoyl]amino]-3-phenylpropanoyl]amino]acetyl]amino]-4-methylpentanoyl]amino]-3-hydroxypropanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-4-methylpentanoic acid
• CAS: 1435677-74-9
• 化学式: C₇₇H₁₀₉N₁₇O₂₀
• 分子量: 1592.81
• InChiKey: YXOZCEQVMZPWOG-YZZULCRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  114
• 可旋转键数：
  34
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  568
• 氢给体数：
  20
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  sungsanpin 、 N-A-(2,4-二硝基-5-氟苯基)-L-丙氨酸 在 盐酸 、 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 反应 1.05h， 生成 (2S,3S)-2-(5-((S)-1-amino-1-oxopropan-2-ylamino)-2,4-dinitrophenylamino)-3-methylpentanoic acid 、 L-FDAA-L-serine 、 L-DAA-L-Leu 、 L-FDAA-L-Pro 、 L-Phe-L-FDAA 、 L-FDAA-L-Lys 、 FDAA-L-Asp 、 L-FDAA-L-Asp-OH
  参考文献：
  名称：

  Sungsanpin, a Lasso Peptide from a Deep-Sea Streptomycete

  摘要：

  Sungsanpin (1), a new 15-amino-acid peptide, was discovered from a Streptomyces species isolated from deep-sea sediment collected off Jeju Island, Korea. The planar structure of 1 was determined by 1D and 2D NMR spectroscopy, mass spectrometry, and UV spectroscopy. The absolute configurations of the stereocenters in this compound were assigned by derivatizations of the hydrolysate of 1 with Marfey's reagents and 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl isothiocyanate, followed by LC-MS analysis. Careful analysis of the ROESY NMR spectrum and three-dimensional structure calculations revealed that sungsanpin possesses the features of a lasso peptide: eight amino acids (-Gly(1)-Phe-Gly-Ser-Lys-Pro-Ile-Asp(8)-) that form a cyclic peptide and seven amino acids (-Ser(9)-Phe-Gly-Leu-Ser-Trp-Leu(15)) that form a tail that loops through the ring. Sungsanpin is thus the first example of a lasso peptide isolated from a marine-derived microorganism. Sungsanpin displayed inhibitory activity in a cell invasion assay with the human lung cancer cell line A549.

  DOI：

  10.1021/np300902g
• 作为产物：
  描述：

  Fmoc-甘氨酸 、 Fmoc-L-亮氨酸 、 Fmoc-L-脯氨酸 、 Fmoc-L-苯丙氨酸 、 FMOC-O-叔丁基-L-丝氨酸 、 Fmoc-L-异亮氨酸 、 N-alpha-芴甲氧羰基-N-epsilon-叔丁氧羰基-L-赖氨酸 、 Fmoc-L-色氨酸(Boc)-OH 、 Fmoc-Asp(O-2-PhⁱPr)-OH 在 3-(4-hydroxymethylphenoxy)propionic acid 、 Wang resin 、 乙酸酐 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 sungsanpin
  参考文献：
  名称：

  套索启发的双环肽：合成，结构和性能

  摘要：

  结合固相和溶液化学方法，描述了受自然套索肽sungsanpin启发的自行车化学合成方法。通过在环和环之间引入共价键来设计双环衍生的拓扑异构体，该共价键允许将肽的这两部分连接在一起，从而形成双环结构。几种结构技术，例如质谱碎裂，离子迁移和NMR光谱分析被用来表征自行车。离子迁移谱研究表明，它表现出类似套索的行为。根据NMR约束预测了其3D结构。另外，自行车的高蛋白水解和热稳定性可能使其成为用于表位移植的合适支架。

  DOI：

  10.1002/chem.201803899

文献信息

• Rational Optimizations of the Marine‐Derived Peptide <i>Sungsanpin</i> as Novel Inhibitors of Cell Invasion
  作者：Anpeng Li、Jihua Zou、Xiaobin Zhuo、Shuai Chen、Xiaoyun Chai、Conghao Gai、Xiang Li、Qingjie Zhao、Yan Zou

  DOI：10.1002/cbdv.202201221

  日期：2023.2

  potential of sungsanpin derivatives as candidates for anti-invasion drugs. We synthesized an analog of sungsanpin (Sun A) using a solid-phase peptide synthesis strategy (SPPS) and further modified its structure to improve its anti-invasion activity. All peptides were tested for their proliferative inhibition and anti-invasion activities in the A549 cell lines. Octapeptide S3 and cyclooctapeptide S4 upregulated

  癌症转移，包括细胞侵袭，是许多癌症患者临床结果不佳和死亡的主要原因。近年来，人们做出了许多努力来从天然衍生的肽中开发有效的治疗分子。Sungsanpin是一种天然衍生的套索肽，可抑制 A549 细胞侵袭。我们旨在评估成三平衍生物作为抗侵袭药物候选物的潜力。我们合成了sungsanpin的类似物(Sun A) 采用固相肽合成策略 (SPPS) 并进一步修饰其结构以提高其抗入侵活性。测试了所有肽在 A549 细胞系中的增殖抑制和抗侵袭活性。八肽S3和环八肽S4有效上调TIMP-1和TIMP-2 mRNA的表达，从而提高对A549细胞侵袭的抑制作用。这两种肽可以抑制高达 60% 的 A549 细胞侵袭，表明它们具有作为开发肽抑制剂的先导分子的潜力。
• A Lasso‐Inspired Bicyclic Peptide: Synthesis, Structure and Properties
  作者：Helena Martin‐Gómez、Fernando Albericio、Judit Tulla‐Puche

  DOI：10.1002/chem.201803899

  日期：2018.12.20

  The chemical synthesis of a bicycle inspired by the natural lasso peptide sungsanpin using a combination of solid‐phase and in‐solution chemistries is described. The bicyclic‐derived topoisomer was designed by introducing a covalent linkage between the ring and the loop, which allowed the tying of these two parts of the peptide, rendering the bicyclic structure. Several structural techniques, such

  结合固相和溶液化学方法，描述了受自然套索肽sungsanpin启发的自行车化学合成方法。通过在环和环之间引入共价键来设计双环衍生的拓扑异构体，该共价键允许将肽的这两部分连接在一起，从而形成双环结构。几种结构技术，例如质谱碎裂，离子迁移和NMR光谱分析被用来表征自行车。离子迁移谱研究表明，它表现出类似套索的行为。根据NMR约束预测了其3D结构。另外，自行车的高蛋白水解和热稳定性可能使其成为用于表位移植的合适支架。
• Sungsanpin, a Lasso Peptide from a Deep-Sea Streptomycete
  作者：Soohyun Um、Young-Joo Kim、Hyuknam Kwon、He Wen、Seong-Hwan Kim、Hak Cheol Kwon、Sunghyouk Park、Jongheon Shin、Dong-Chan Oh

  DOI：10.1021/np300902g

  日期：2013.5.24

  Sungsanpin (1), a new 15-amino-acid peptide, was discovered from a Streptomyces species isolated from deep-sea sediment collected off Jeju Island, Korea. The planar structure of 1 was determined by 1D and 2D NMR spectroscopy, mass spectrometry, and UV spectroscopy. The absolute configurations of the stereocenters in this compound were assigned by derivatizations of the hydrolysate of 1 with Marfey's reagents and 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl isothiocyanate, followed by LC-MS analysis. Careful analysis of the ROESY NMR spectrum and three-dimensional structure calculations revealed that sungsanpin possesses the features of a lasso peptide: eight amino acids (-Gly(1)-Phe-Gly-Ser-Lys-Pro-Ile-Asp(8)-) that form a cyclic peptide and seven amino acids (-Ser(9)-Phe-Gly-Leu-Ser-Trp-Leu(15)) that form a tail that loops through the ring. Sungsanpin is thus the first example of a lasso peptide isolated from a marine-derived microorganism. Sungsanpin displayed inhibitory activity in a cell invasion assay with the human lung cancer cell line A549.