N-叔丁氧羰基-D-阿拉伯型-N-甲基异亮氨酸 | 53462-50-3

• 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
• 中文名称: N-叔丁氧羰基-D-阿拉伯型-N-甲基异亮氨酸
• 英文名称: N-Boc-(2R,3S)-N-Me-Ile
• 英文别名: Boc-N-Me-D-Allo-Ile-OH；(2R,3S)-3-methyl-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]pentanoic acid
• CAS: 53462-50-3
• 化学式: C₁₂H₂₃NO₄
• 分子量: 245.319
• InChiKey: HTBIAUMDQYXOFG-DTWKUNHWSA-N

物化性质

• 沸点：
  338.2±21.0 °C(Predicted)
• 密度：
  1.053±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-叔丁氧羰基-D-阿拉伯型-N-甲基异亮氨酸 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 N-甲基-D-别异亮氨酸
  参考文献：
  名称：

  Highly N-Methylated Linear Peptides Produced by an Atypical Sponge-Derived Acremonium sp.

  摘要：

  RHM1 (1) and RHM2 (2) are highly N-methylated linear octapeptides produced by an atypical strain of Acremonium sp., cultured from a marine sponge collected in Papua New Guinea. The known peptaibiotic efrapeptin G (3) was also isolated from this fungus. The planar structures of 1 and 2 were assigned based on 1D- and 2D-NMR experiments and fragmentation patterns from ESIMS. The absolute configuration of 1 was determined via Marfey's method; the absolute configuration of 2 is proposed to be identical. Efrapeptin G (3) displayed potent cytotoxicity against murine cancer cell lines. while RHMI (1) and RHM2 (2) showed weak cytotoxicity against murine cancer cell lines; efrapeptin G (3) and RHMI (1) also demonstrated antibacterial activity.

  DOI：

  10.1021/np0503653
• 作为产物：
  描述：

  N-叔丁氧羰基-D-别异亮氨酸 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 生成 N-叔丁氧羰基-D-阿拉伯型-N-甲基异亮氨酸
  参考文献：
  名称：

  Trichormamides A and B with Antiproliferative Activity from the Cultured Freshwater CyanobacteriumTrichormussp. UIC 10339

  摘要：

  Two new cyclic lipopeptides, trichormamides A (1) and B (2), were isolated from the cultured freshwater cyanobacterium Trichormus sp. UIC 10339. The strain was obtained from a sample collected in Raven Lake in Northern Wisconsin. The planar structures of trichormamides A (1) and B (2) were determined using a combination of spectroscopic analyses including HRESIMS and 1D and 2D NMR experiments. The absolute configurations of the amino acid residues were assigned by the advanced Marfey's method after acid hydrolysis. Trichormamide A (1) is a cyclic undecapeptide containing two D-amino acid residues (D-Tyr and D-Leu) and one beta-amino acid residue (beta-aminodecanoic acid). Trichormamide B (2) is a cyclic dodecapeptide characterized by the presence of four nonstandard alpha-amino acid residues (homoserine, N-methylisoleucine, and two 3-hydroxyleucines) and one beta-amino acid residue (beta-aminodecanoic acid). Trichormamide B (2) was cytotoxic against MDA-MB-435 and HT-29 cancer cell lines with IC50 values of 0.8 and 1.5 mu M, respectively.

  DOI：

  10.1021/np5003548

文献信息

• Isolation, Structure Determination, and Total Synthesis of Hoshinoamide C, an Antiparasitic Lipopeptide from the Marine Cyanobacterium <i>Caldora penicillata</i>
  作者：Arihiro Iwasaki、Keisuke Ohtomo、Naoaki Kurisawa、Ikuma Shiota、Yulia Rahmawati、Ghulam Jeelani、Tomoyoshi Nozaki、Kiyotake Suenaga

  DOI：10.1021/acs.jnatprod.0c01209

  日期：2021.1.22

  we synthesized two possible diastereomers of hoshinoamide C and determined its absolute configuration based on a comparison of their spectroscopic data with those of the natural compound. Hoshinoamide C (1) did not exhibit any cytotoxicity against HeLa or HL60 cells at 10 μM, but inhibited the growth of the parasites responsible for malaria (IC50 0.96 μM) and African sleeping sickness (IC50 2.9 μM)

  Hoshinoamide C ( 1 ) 是一种抗寄生虫脂肽，是从海洋蓝藻Caldora penicillata 中分离出来的。其平面结构通过光谱分析（主要是 2D NMR）阐明，α-氨基酸部分的绝对构型通过降解反应和手性相 HPLC 分析确定。为了阐明不寻常氨基酸部分的绝对构型，我们合成了星野酰胺 C 的两种可能的非对映异构体，并根据光谱数据与天然化合物的光谱数据的比较确定了其绝对构型。Hoshinoamide C ( 1 ) 在 10 μM 时对 HeLa 或 HL60 细胞没有表现出任何细胞毒性，但抑制了导致疟疾的寄生虫的生长 (IC 500.96 μM) 和非洲昏睡病 (IC 50 2.9 μM)。
• Highly <i>N</i>-Methylated Linear Peptides Produced by an Atypical Sponge-Derived <i>Acremonium</i> sp.
  作者：Claudia M. Boot、Karen Tenney、Frederick A. Valeriote、Phillip Crews

  DOI：10.1021/np0503653

  日期：2006.1.1

  RHM1 (1) and RHM2 (2) are highly N-methylated linear octapeptides produced by an atypical strain of Acremonium sp., cultured from a marine sponge collected in Papua New Guinea. The known peptaibiotic efrapeptin G (3) was also isolated from this fungus. The planar structures of 1 and 2 were assigned based on 1D- and 2D-NMR experiments and fragmentation patterns from ESIMS. The absolute configuration of 1 was determined via Marfey's method; the absolute configuration of 2 is proposed to be identical. Efrapeptin G (3) displayed potent cytotoxicity against murine cancer cell lines. while RHMI (1) and RHM2 (2) showed weak cytotoxicity against murine cancer cell lines; efrapeptin G (3) and RHMI (1) also demonstrated antibacterial activity.
• Trichormamides A and B with Antiproliferative Activity from the Cultured Freshwater Cyanobacterium<i>Trichormus</i>sp. UIC 10339
  作者：Shangwen Luo、Aleksej Krunic、Hahk-Soo Kang、Wei-Lun Chen、John L. Woodard、James R. Fuchs、Steven M. Swanson、Jimmy Orjala

  DOI：10.1021/np5003548

  日期：2014.8.22

  Two new cyclic lipopeptides, trichormamides A (1) and B (2), were isolated from the cultured freshwater cyanobacterium Trichormus sp. UIC 10339. The strain was obtained from a sample collected in Raven Lake in Northern Wisconsin. The planar structures of trichormamides A (1) and B (2) were determined using a combination of spectroscopic analyses including HRESIMS and 1D and 2D NMR experiments. The absolute configurations of the amino acid residues were assigned by the advanced Marfey's method after acid hydrolysis. Trichormamide A (1) is a cyclic undecapeptide containing two D-amino acid residues (D-Tyr and D-Leu) and one beta-amino acid residue (beta-aminodecanoic acid). Trichormamide B (2) is a cyclic dodecapeptide characterized by the presence of four nonstandard alpha-amino acid residues (homoserine, N-methylisoleucine, and two 3-hydroxyleucines) and one beta-amino acid residue (beta-aminodecanoic acid). Trichormamide B (2) was cytotoxic against MDA-MB-435 and HT-29 cancer cell lines with IC50 values of 0.8 and 1.5 mu M, respectively.