(2S,3R)-Amha

• 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,3R)-Amha
• 英文别名: (2S,3R)-3-amino-2-methylhexanoic acid；3-amino-2-methylhexanoic acid；AMHA
• 化学式: C₇H₁₅NO₂
• 分子量: 145.202
• InChiKey: YUTPPOMETNXNNX-NTSWFWBYSA-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：

  (2S,3R)-Amha 在 氯化亚砜 、 碳酸氢钠 作用下， 以 乙酸乙酯 为溶剂， 反应 28.0h， 生成 (2S,3R)-methyl 3-(((benzyloxy)carbonyl)amino)-2-methylhexanoate
  参考文献：
  名称：

  Enantioselective Aldehyde α-Nitroalkylation via Oxidative Organocatalysis

  摘要：

  The first enantioselective organocatalytic alpha-nitroatkylation of aldehydes has been accomplished. The aforementioned process involves the oxidative coupling of an enamine intermediate, generated transiently via condensation of an amine catalyst with an aldehyde, with a silyl. nitronate to produce a beta-nitroaldehyde. Two methods, one that furnishes the syn beta-nitroaldehyde and a second that provides access to the anti isomer, have been developed. Data are presented to support a hypothesis that explains this phenomenon in terms of a silyl group-controlled change in mechanism. Finally, a three-step procedure for the synthesis of both syn- and anti-alpha,beta-disubstituted beta-amino acids is presented.

  DOI：

  10.1021/ja904504j
• 作为产物：
  描述：

  (4S,2'S,3'R)-3-[3'-((4''-toluenesulfonyl)oxy)-2'-methylhexanoyl]-4-isopropyl-2-oxazolidinone 在 sodium azide 、 15-冠醚-5 、 lithium hydroxide monohydrate 、 氢气 、 双氧水 、 lithium bromide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 4.0h， 生成 (2S,3R)-Amha
  参考文献：
  名称：

  Enantioselective Aldehyde α-Nitroalkylation via Oxidative Organocatalysis

  摘要：

  The first enantioselective organocatalytic alpha-nitroatkylation of aldehydes has been accomplished. The aforementioned process involves the oxidative coupling of an enamine intermediate, generated transiently via condensation of an amine catalyst with an aldehyde, with a silyl. nitronate to produce a beta-nitroaldehyde. Two methods, one that furnishes the syn beta-nitroaldehyde and a second that provides access to the anti isomer, have been developed. Data are presented to support a hypothesis that explains this phenomenon in terms of a silyl group-controlled change in mechanism. Finally, a three-step procedure for the synthesis of both syn- and anti-alpha,beta-disubstituted beta-amino acids is presented.

  DOI：

  10.1021/ja904504j

文献信息

• 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
• 顺式β-氨基酸及其衍生物的合成方法
  申请人：北京大学深圳研究生院

  公开号：CN109776342A

  公开（公告）日：2019-05-21

  本发明属于合成化学技术领域，具体涉及一种顺式β‑氨基酸及其衍生物的合成方法。本发明所提供的合成方法，包括如下步骤：提供如式a所示的N‑酰基噁唑烷酮，如式b所示的亚磺酰亚胺，以及碱性催化剂，其中，所述N‑酰基噁唑烷酮的4位碳的R、S构型与所述亚磺酰亚胺的磺酰基硫的R、S构型相反；将所述N‑酰基噁唑烷酮与所述亚磺酰亚胺混合，并在所述碱性催化剂的催化作用下发生不对称加成反应，得到如式c1或式c2所示的顺式β氨基酸前体；将所述顺式β氨基酸前体进行水解和官能团转化，得到如式d所示的顺式β氨基酸及其衍生物。
• 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。
• An azumamide C analogue without the zinc-binding functionality
  作者：Jesper S. Villadsen、Betül Kitir、Kathrine Wich、Tina Friis、Andreas S. Madsen、Christian A. Olsen

  DOI：10.1039/c4md00252k

  日期：——

  Histone deacetylase (HDAC) inhibitors have attracted considerable attention due to their promise as therapeutic agents.

  组蛋白去乙酰化酶（HDAC）抑制剂因其作为治疗药物的潜力而受到广泛关注。
• Kakeromamide A, a new cyclic pentapeptide inducing astrocyte differentiation isolated from the marine cyanobacterium Moorea bouillonii
  作者：Fumiaki Nakamura、Hiroshi Maejima、Midori Kawamura、Daisuke Arai、Tatsufumi Okino、Meng Zhao、Tao Ye、Jungyeol Lee、Young-Tae Chang、Nobuhiro Fusetani、Yoichi Nakao

  DOI：10.1016/j.bmcl.2018.04.067

  日期：2018.7

  Kakeromamide A (1), a new cyclic pentapeptide encompassing a thiazole ring moiety and a beta-amino acid, was isolated from the marine cyanobacterium Moorea bouillonii. Its structure was elucidated by the spectral analysis and the modified Marfey's method. Compound 1 induced differentiation of neural stem cells into astrocytes at the concentration of 10 mu M. (C) 2018 Published by Elsevier Ltd.