(2S)-2-(2-(tert-butoxycarbonylamino)-4-(methylthio)butanamido)-4-methylpentanoic acid | 33014-87-8

• 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-(tert-butoxycarbonylamino)-4-(methylthio)butanamido)-4-methylpentanoic acid
• 英文别名: Boc-L-Met-L-Leu-OH；Boc-Met-Leu-OH；Boc-Met-Leu；(2S)-4-methyl-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-methylsulfanylbutanoyl]amino]pentanoic acid
• CAS: 33014-87-8
• 化学式: C₁₆H₃₀N₂O₅S
• 分子量: 362.491
• InChiKey: XMZUESJXUFGXQI-RYUDHWBXSA-N

物化性质

• 熔点：
  127-129 °C
• 沸点：
  577.7±50.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  130
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S)-2-(2-(tert-butoxycarbonylamino)-4-(methylthio)butanamido)-4-methylpentanoic acid 在 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 甲基(2S)-2-[[(2S)-4-甲基-2-[[(2S)-2-[(2-甲基丙烷-2-基)氧基羰基氨基]-4-甲硫基丁酰基]氨基]戊酰]氨基]-3-苯丙酸酯
  参考文献：
  名称：

  Chemo-Enzymatic Synthesis of Fmoc-Peptide Fragments

  摘要：

  Optically pure Fmoc-peptide fragments have been prepared via dicyclohexylcarbodiimide coupling of N-protected amino acids with amino acid esters, followed by enzyme-catalyzed ester hydrolysis by alcalase with a high concentration of organic solvent in a high yield.

  DOI：

  10.1080/00397919208055416
• 作为产物：
  描述：

  Boc-L-蛋氨酸 在 水 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (2S)-2-(2-(tert-butoxycarbonylamino)-4-(methylthio)butanamido)-4-methylpentanoic acid
  参考文献：
  名称：

  含有对位取代的Phe残基的新型活性For-Met-Leu-Phe-OMe类似物的合成和生物学评估。

  摘要：

  在本研究中，我们报告了N -Boc保护的三肽4a-1和N-保护的三肽5a-1作为新的For-Met-Leu-Phe-OMe（fMLF-OMe）类似物的合成和生物学评估。所有这些新的配体都以在芳环第4位被不同取代的C端Phe残基为特征。已经对人类嗜中性白细胞检查了5a-1的激动作用和4a-1的拮抗作用（趋化性，超氧阴离子的产生，溶菌酶的释放以及受体结合亲和力）。尽管化合物5a和5a和5b的合成化学作用均没有比标准的fMLF-OMe三肽更高的活性。在芳环上第4位分别带有-CH 3和-C（CH 3）3的5c优于标准三肽，以更高的浓度刺激超氧阴离子的产生。化合物4f和4i分别在苯丙氨酸的芳环上的4位含有-F和-I，表现出显着的趋化拮抗作用。讨论了位置4不同取代对苯丙氨酸芳环的影响。版权所有©2012欧洲肽协会和John Wiley＆Sons，Ltd.

  DOI：

  10.1002/psc.2414

文献信息

• Phase-transfer reagents as C-terminal protecting groups; facile incorporation of free amino acids or peptides into peptide sequences
  作者：Shui-Tein Chen、Kung-Tsung Wang

  DOI：10.1039/c39900001045

  日期：——

  Phase-transfer reagents (basic, neutral, and acidic) can effect temporary protection of carboxy groups by salt formation in C-terminal free amino acids or peptides during peptide synthesis; the use of acidic or neutral phase-transfer reagents as the C-terminal protecting group will not affect the nucleophilicity of the amino group of the salts thus prepared in an organic solvent.

  相转移试剂（碱性，中性和酸性）可通过在肽合成过程中在C端游离氨基酸或肽中形成盐来暂时保护羧基。使用酸性或中性相转移试剂作为C-末端保护基不会影响在有机溶剂中如此制得的盐的氨基的亲核性。
• Synthesis and Biological Evaluation of Curcumin Derivatives with Water-Soluble Groups as Potential Antitumor Agents: An in Vitro Investigation Using Tumor Cell Lines
  作者：Luyang Ding、Shuli Ma、Hongxiang Lou、Longru Sun、Mei Ji

  DOI：10.3390/molecules201219772

  日期：——

  Three series of curcumin derivatives including phosphorylated, etherified, and esterified products of curcumin were synthesized, and their anti-tumor activities were assessed against human breast cancer MCF-7, hepatocellular carcinoma Hep-G2, and human cervical carcinoma HeLa cells. Compared with curcumin, compounds 3, 8, and 9 exhibited stronger antitumor cell line growth activities against HeLa cells. Compound 12 also showed higher antitumor cell line growth activities on MCF-7 cells than curcumin. Among them, 4-((1E,6E)-7-(4-Hydroxy-3-methoxyphenyl)-3,5-dioxohepta-1,6-dienyl)-2-methoxyphenyl dihydrogen phosphate(3) showed the strongest activity with an half maximal inhibitory concentration (IC50) of 6.78 µM against HeLa cells compared with curcumin with an IC50 of 17.67 µM. Stabilities of representatives of the three series were tested in rabbit plasma in vitro, and compounds 3 and 4 slowly released curcumin in plasma. The effect of compound 3 on HeLa cell apoptosis was determined by examining morphological changes by DAPI (4′,6-diamidino-2-phenylindole) staining as well as Annexin V-FITC/ Propidium Iodide (PI) double staining and flow cytometry. The results showed that 3 induced cellular apoptosis in a dose-dependent manner. Together our findings show that 3 merits further investigation as a new potential antitumor drug candidate.

  合成了三类姜黄素衍生物，包括磷酸化、醚化和酯化的姜黄素产品，并评估了它们对人乳腺癌MCF-7、肝细胞癌Hep-G2和人宫颈癌HeLa细胞的抗肿瘤活性。与姜黄素相比，化合物3、8和9在对HeLa细胞的抗肿瘤细胞生长活性方面表现出更强的活性。化合物12在MCF-7细胞上的抗肿瘤细胞生长活性也高于姜黄素。其中，化合物4-((1E,6E)-7-(4-羟基-3-甲氧基苯基)-3,5-二氧杂庚-1,6-二烯基)-2-甲氧基苯基二氢磷酸(3)表现出最强的活性，对HeLa细胞的半最大抑制浓度(IC50)为6.78 µM，而姜黄素的IC50为17.67 µM。在体外测试了这三类代表化合物在兔血浆中的稳定性，化合物3和4在血浆中缓慢释放姜黄素。通过DAPI（4′,6-二氨基-2-苯基吲哚）染色以及Annexin V-FITC/碘化丙锭（PI）双重染色和流式细胞术，确定了化合物3对HeLa细胞凋亡的影响。结果显示，化合物3以剂量依赖的方式诱导细胞凋亡。综上所述，我们的研究结果表明，化合物3值得进一步研究作为新的潜在抗肿瘤药物候选者。
• New fMLF-OMe Analogues Containing Constrained Mimics of Phenylalanine Residue
  作者：Ines Torrini、Gaia Mastropietro、Giampiero Pagani Zecchini、Mario Paglialunga Paradisi、Gino Lucente、Susanna Spisani

  DOI：10.1002/(sici)1521-4184(199805)331:5<170::aid-ardp170>3.0.co;2-b

  日期：1998.5

  different analogues of the native ligand have been synthesized and evaluated. Compounds 1‐3 possess the general formula HCO‐Met‐Leu‐Xaa‐OMe with Xaa = N‐benzylglycine, N‐benzylphenylalanine, and α,α‐dibenzylglycine, respectively. In the analogue 4 the constraint at the C‐terminus has been obtained by incorporating a 2‐oxopiperazine ring, made up of two phenylalanine residues, to replace the native

  在一项旨在阐明 HCO-Met-Leu-Phe-OMe (fMLF-OMe) 结构特征的研究项目中，该结构特征控制与 C-末端残基对应的受体的相互作用，天然配体的四种不同类似物具有被合成和评估。化合物 1-3 的通式为 HCO-Met-Leu-Xaa-OMe，其中 Xaa = N-苄基甘氨酸、N-苄基苯丙氨酸和 α, α-二苄基甘氨酸。在类似物 4 中，通过引入由两个苯丙氨酸残基组成的 2-氧代哌嗪环来取代天然的 C-末端 Phe 残基，从而获得了 C-末端的约束。讨论了化学修饰对新类似物活性的影响。
• Selective C−H Acyloxylation of Sulfides/Disulfides Enabled by Hypervalent Iodine Reagents
  作者：Shuang Wu、Yiyun Chen

  DOI：10.1002/adsc.202300360

  日期：2023.8.15

  Herein, we report the α−C−H acyloxylation of sulfides and disulfides enabled by hypervalent iodine(III) reagents via photoredox catalysis. The methoxylbenziodoxole derivatives serve as the hydrogen atom transfer agent, the mild oxidant, and the acyloxylation source in the reaction. External nucleophiles can also be introduced to the α−C−H of sulfides. The reaction applies to various aryl and alkyl

  在此，我们报道了高价碘 (III) 试剂通过光氧化还原催化实现硫化物和二硫化物的 α−C−H 酰氧基化。甲氧基苯并杂环戊烯衍生物在反应中充当氢原子转移剂、温和氧化剂和酰氧基化源。外部亲核试剂也可以引入到硫化物的 α−C−H 中。该反应适用于各种芳基硫醚和烷基硫醚，包括蛋氨酸肽衍生物。二硫化物首次应用，具有优异的化学选择性和官能团相容性。
• β-Peptido sulfonamides: for-Met-Leu-Phe-OMe analogues containing taurine and chiral β-amino-ethanesulfonic acid residues
  作者：Cesare Giordano、Marianna Nalli、Mario Paglialunga Paradisi、Anna Sansone、Gino Lucente、Susanna Spisani

  DOI：10.1016/j.farmac.2004.07.014

  日期：2004.12

  A series of new beta-peptido sulfonamides, related to the chemotactic tripeptide fMLF-OMe, has been synthesized. The examined 1a,b-7a,b models contain the achiral -HN-(CH(2))(2)-SO(2)- taurine (Tau) residue or the chiral -HN-CH(nBu)-CH(2)-SO(2)- and -HN-CH(iBu)-CH(2)-SO(2)- residues, corresponding to the beta-aminocarboxylic acid counterparts beta(3)-HNle and beta(3)-HLeu, respectively. The biological activity of the new analogues has been determined on human neutrophils and compared with that of the reference ligand as well as that of the previously studied related models. The results are analyzed in terms of structure-activity relationships. The conformational preferences of the new tripeptides 1b and 2b, containing a central chiral beta-amino-ethanesulfonic acid residue, have also been discussed.