(2R,3R)-3-amino-2-methylhexanoic acid | 410087-14-8

• 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: (2R,3R)-3-amino-2-methylhexanoic acid
• 英文别名: 3-amino-2-methylhexanoic acid；(2R,3R)-Amha；AMHA
• CAS: 410087-14-8
• 化学式: C₇H₁₅NO₂
• 分子量: 145.202
• InChiKey: YUTPPOMETNXNNX-PHDIDXHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3R)-3-amino-2-methylhexanoic acid 在 4-二甲氨基吡啶 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 16.0h， 生成 benzyl (2R,3R)-3-amino-2-methylhexanoyl-L-lactic acid
  参考文献：
  名称：

  ulongamide A的全合成，一种从海洋蓝细菌Lyngbya sp。分离的环状二肽。

  摘要：

  ulongamide A（1）是一种具有细胞毒性的天然环状二肽肽，是通过一条收敛性路线实现的，该路线涉及将片段7和8与五肽24偶联，然后在先去除t- Boc保护基团之后将其环化。

  DOI：

  10.1016/j.tetlet.2006.11.117
• 作为产物：
  描述：

  (4R,5S,2'R,3'R)-3-(3'-azido-2'-methylhexanoyl)-5-phenyl-4-methyl-2-oxazolidinone 在 palladium on activated charcoal lithium hydroxide 、 氢气 、 双氧水 作用下， 以 甲醇 、 水 为溶剂， 生成 (2R,3R)-3-amino-2-methylhexanoic acid
  参考文献：
  名称：

  ulongamide A的全合成，一种从海洋蓝细菌Lyngbya sp。分离的环状二肽。

  摘要：

  ulongamide A（1）是一种具有细胞毒性的天然环状二肽肽，是通过一条收敛性路线实现的，该路线涉及将片段7和8与五肽24偶联，然后在先去除t- Boc保护基团之后将其环化。

  DOI：

  10.1016/j.tetlet.2006.11.117

文献信息

• Total synthesis of ulongamide A, a cyclic depsipeptide isolated from marine cyanobacteria Lyngbya sp.
  作者：Cuauhtémoc Alvarado、Eduardo Díaz、Ángel Guzmán

  DOI：10.1016/j.tetlet.2006.11.117

  日期：2007.1

  A total synthesis of ulongamide A (1), a cytotoxic natural cyclic depsipeptide, was achieved by a convergent route involving coupling of the fragments 7 and 8 to the pentapeptide 24, and subsequent cyclization thereof after prior removal of the t-Boc protecting groups.

  ulongamide A（1）是一种具有细胞毒性的天然环状二肽肽，是通过一条收敛性路线实现的，该路线涉及将片段7和8与五肽24偶联，然后在先去除t- Boc保护基团之后将其环化。
• Halogenated Fatty Acid Amides and Cyclic Depsipeptides from an Eastern Caribbean Collection of the Cyanobacterium <i>Lyngbya majuscula</i>
  作者：Jorge I. Jiménez、Tifanie Vansach、Wesley Y. Yoshida、Bryan Sakamoto、Peter Pörzgen、F. David Horgen

  DOI：10.1021/np900173d

  日期：2009.9.25

  extract of an eastern Caribbean collection of Lyngbya majuscula yielded two new halogenated fatty acid amides, grenadamides B (1) and C (2), and two new depsipeptides, itralamides A (3) and B (4), along with the known compounds hectochlorin and deacetylhectochlorin. The recently reported depsipeptide carriebowmide (5) was also present in the extract and isolated as its sulfone artifact (6). Compounds 1−4

  东加勒比收集的Lyngbya majuscula的亲脂性提取物产生了两种新的卤代脂肪酸酰胺，手榴弹胺 B ( 1 ) 和 C ( 2 )，以及两种新的缩肽，依曲酰胺 A ( 3 ) 和 B ( 4 )，以及已知的化合物八氯环素和脱乙酰八氯环素。最近报道的缩酚肽 carriebowmide ( 5 ) 也存在于提取物中，并作为其砜类人工制品被分离 ( 6 )。化合物1 - 4通过光谱方法鉴定。3 , 4 , 6氨基酸残基的构型通过酸水解产物的非对映异构衍生物的 LC-MS 分析（高级 Marfey 方法）确定。基于6的构型分析，与真正的carriebowmide ( 5 )直接比较，提出了对5的微小结构修正。化合物1和2对甜菜夜蛾（Spodoptera exigua）显示出边际活性。化合物1 - 4和6进行了评估在人胚胎肾（HEK293）细胞一般小区毒性。只有依曲酰胺 B ( 4 ) 显示出显着的细胞毒性，IC
• Carriebowmide, a New Cyclodepsipeptide from the Marine Cyanobacterium <i>Lyngbya</i> <i>polychroa</i>
  作者：Sarath P. Gunasekera、Raphael Ritson-Williams、Valerie J. Paul

  DOI：10.1021/np800453t

  日期：2008.12.26

  acids, 3-amino-2-methylhexanoic acid and methionine sulfoxide, was isolated from the fish-deterrent lipophilic extract of the marine cyanobacterium Lyngbya polychroa, collected from the fore reef near the Smithsonian field station at Carrie Bow Cay, Belize. Its planar structure was determined by NMR spectroscopic techniques. The absolute stereochemistry of the hydroxy acid and all R-aminoacid-derived units

  新的环二肽肽carriebowmide包含两个稀有氨基酸3-氨基-2-甲基己酸和蛋氨酸亚砜，是从海洋蓝藻Lyngbya polychroa的具有鱼类威慑力的脂溶性提取物中分离出来的，该提取物是从Smithsonian野外站附近的前礁收集的。在伯利兹的Carrie Bow Cay。通过NMR光谱技术确定其平面结构。通过酸水解产物的手性HPLC分析确定了羟基酸和所有R-氨基酸衍生的单元的绝对立体化学。β-氨基酸部分的3-氨基-2-甲基己酸的立体化学是通过酸水解产物的马菲分析确定的。
• Kulokekahilide-1, a Cytotoxic Depsipeptide from the Cephalaspidean Mollusk <i>Philinopsis speciosa</i>
  作者：Junji Kimura、Yuuki Takada、Tomoko Inayoshi、Yoichi Nakao、Gilles Goetz、Wesley Y. Yoshida、Paul J. Scheuer

  DOI：10.1021/jo010176z

  日期：2002.3.1

  The cytotoxic depsipeptide kulokekahilide-1, which contains two unusual amino acids, 4-phenylvaline and 3-amino-2-methylhexanoic acid, was isolated from the cephalaspidean mollusk Philinopsis speciosa. Structure elucidation of kulokekahilide-1 was carried out by spectroscopic analysis and chemical degradation. The absolute stereochemistry was determined by Marfey analysis for amino acids and chiral HPLC analysis for hydroxy acids. All four stereoisomers of 4-phenylvaline and 3-amino-2-methylhexanoic acid, which were necessary for Marfey analysis, were synthesized by use of the Heck reaction and Evans's method, respectively. Kulokekahilide-1 showed cytotoxicity against P388 murine leukemia cells with an IC50 value of 2.1 mug/mL.
• Cyclic Depsipeptides, Grassypeptolides D and E and Ibu-epidemethoxylyngbyastatin 3, from a Red Sea <i>Leptolyngbya</i> Cyanobacterium
  作者：Christopher C. Thornburg、Muralidhara Thimmaiah、Lamiaa A. Shaala、Andrew M. Hau、Jay M. Malmo、Jane E. Ishmael、Diaa T. A. Youssef、Kerry L. McPhail

  DOI：10.1021/np200270d

  日期：2011.8.26

  Two new grassypeptolides and a lyngbyastatin analogue, together with the known dolastatin 12, have been isolated from field collections and laboratory cultures of the marine cyanobacterium Leptolyngbya sp. collected from the SS Thistlegorm shipwreck in the Red Sea. The overall stereostructures of grassypeptolides D (1) and E (2) and Ibu-epidemethoxylyngbyastatin 3 (3) were determined by a combination of 1D and 2D NMR experiments, MS analysis, Marfey's methodology, and HPLC-MS. Compounds 1 and 2 contain 2-methyl-3-aminobutyric acid and 2-aminobutyric acid, while biosynthetically distinct 3 contains 3-amino-2-methylhexanoic acid and the beta-keto amino acid 4-amino-2,2-dimethyl-3-oxopentanoic acid (Ibu). Grassypeptolides D (1) and E (2) showed significant cytotoxicity to HeLa (IC50 = 335 and 192 nM, respectively) and mouse neuro-2a blastoma cells (IC50 = 599 and 407 nM, respectively), in contrast to Ibu-epidemethoxylyngbyastatin 3 (neuro-2a cells, IC50 > 10 mu M) and dolastatin 12 (neuro-2a cells, IC50 > 1 mu M).