2-甲基半胱氨酸 | 239101-34-9

• 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: 2-甲基半胱氨酸
• 中文别名: D-半胱氨酸,2-甲基-
• 英文名称: (S)-α-methyl cysteine
• 英文别名: (S)-α-methylcysteine；(S)-2-methyl cysteine；2-methyl-D-cysteine；(S)-2-methylcysteine；2-methyl L-cysteine；(S)-alpha-Methylcysteine；(2S)-2-amino-2-methyl-3-sulfanylpropanoic acid
• CAS: 239101-34-9
• 化学式: C₄H₉NO₂S
• mdl: MFCD10687068
• 分子量: 135.187
• InChiKey: NZBONMFLYFGTAC-SCSAIBSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  64.3
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-甲基半胱氨酸 在 甲酸 、 双氧水 作用下， 以 水 为溶剂， 反应 2.0h， 生成 (S)-2-methylcysteic acid
  参考文献：
  名称：

  Cyclic Depsipeptides, Grassypeptolides D and E and Ibu-epidemethoxylyngbyastatin 3, from a Red Sea Leptolyngbya Cyanobacterium

  摘要：

  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).

  DOI：

  10.1021/np200270d
• 作为产物：
  描述：

  (S)-2,2,4-trimethylthiazolidine-4-carboxamide 在 水 作用下， 反应 3.0h， 以95%的产率得到
  参考文献：
  名称：

  PROCESS FOR PRODUCING OPTICALLY ACTIVE 2-ALKYLCYSTEINE, DERIVATIVE THEREOF, AND PROCESSES FOR PRODUCTION

  摘要：

  公开号：

  EP1686114B1

文献信息

• Efficient Asymmetric Synthesis of (<i>S</i>)- and (<i>R</i>)-<i>N</i>-Fmoc-<i>S</i>-Trityl-α-methylcysteine Using Camphorsultam as a Chiral Auxiliary
  作者：Satendra Singh、Samala J. Rao、Michael W. Pennington

  DOI：10.1021/jo049622j

  日期：2004.6.1

  resulting in the formation of (S)-α-methylcysteine from (1R)-(+)-2,10-camphorsultam and (R)-α-methylcysteine from (1S)-(−)-2,10-camphorsultam after acidic hydrolysis. Subsequent protection of the side chain thiol group with trityl alcohol and α-amine function with Fmoc-OSu furnished fully protected (S)- and (R)-N-Fmoc-S-trityl-α-methylcysteine in overall 20% yield.

  将（1 R）-（+）-2,10-和（1 S）-（-）-2,10-樟脑酰胺用2-苯基噻唑啉4-羧酸乙酯酰化，得到（+）-和（-）-2 -苯基噻唑啉基樟脑磺酰胺，其在正丁基锂存在下用MeI立体选择性地烷基化。这些苯基噻唑啉基樟脑苏丹草的烷基化反应是从β面而不是α面发生的，从而导致从（1 R）-（+）-2,10-樟脑苏丹草和（R）-α-形成（S）-α-甲基半胱氨酸酸性水解后的（1 S）-（-）-2,10-樟脑磺胺中的甲基半胱氨酸。Fmoc-OSu提供的三苯甲基醇和α-胺官能团可随后对侧链硫醇基团进行全面保护（S） -和（- [R ）- ñ -Fmoc-小号三苯-α甲基半胱氨酸在总产率为20％。
• Effects of C-4 Stereochemistry and C-4‘ Hydroxylation on the Iron Clearing Efficiency and Toxicity of Desferrithiocin Analogues
  作者：Raymond J. Bergeron、Jan Wiegand、James S. McManis、Bruce H. McCosar、William R. Weimar、Gary M. Brittenham、Richard E. Smith

  DOI：10.1021/jm990058s

  日期：1999.7.1

  S)-carboxylic acid. The stereochemistry at C-4 is shown to have a substantial effect on the iron clearing efficiency of desferrithiocin analogues, as does C-4'-hydroxylation on the toxicity profile. All of the compounds are evaluated in a bile-duct-cannulated rodent model to determine iron clearance efficiency and are carried forward to the iron-overloaded primate for iron clearing measurements. On

  进行了去铁硫霉素类似物的其他结构活性研究。使用对映体4,5-二氢-2-（2,4-二羟基苯基）噻唑-4（R）-羧酸和4,5对映体评估和评估C-4上立体化学对配体铁清除效率的影响-二氢-2-（2,4-二羟基苯基）噻唑-4（S）-羧酸。还通过4，5-二氢-2-（2-羟苯基）-4-甲基噻唑-4（S）的合成和体内比较进一步研究了4'-羟基化作为降低脱氮杂脱铁硫霉素类似物毒性的方法的实用性。 ）-羧酸，它是天然产物4-甲基芥子酸，和4，5-二氢-2-（2,4-二羟基苯基）-4-甲基噻唑-4（S）-羧酸。C-4处的立体化学显示对去铁硫代类似物的铁清除效率有实质性影响，C-4'-羟基化对毒性谱也有显着影响。所有化合物均在胆管插管的啮齿动物模型中进行评估，以确定铁清除效率，并将其运用于重载铁的灵长类动物中进行铁清除测试。根据当前工作的结果，尽管4,5-二氢-2-（2,4-二羟基苯基）噻唑-4（S）-羧酸仍然是临床评估中最有希望的候选药物，但是4
• Process for the preparation of substituted thiazolines and their intermediates
  申请人：Krich Sylvia

  公开号：US20050101782A1

  公开（公告）日：2005-05-12

  Process for the preparation of substituted thiazolines of the formula (I) in which Ar is a phenyl, naphthyl, thienyl, pyridyl or quinolinyl radical which can optionally be substituted by one or more substituents from the group consisting of halogen, OH, benzyloxy, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, COOR 1 where R 1 is H or C 1 -C 4 -alkyl, by coupling of (S)-α-methylcysteine hydrochloride of the formula (II) with a nitrile of the formula (III) Ar—CN in which Ar is as defined above, or a corresponding C 1 -C 4 -alkyl imidate, in which (S)-α-methylcysteine hydrochloride of the formula (II) is reacted in a suitable solvent with a nitrile of the formula (III) or a corresponding C 1 -C 4 -alkyl imidate in the presence of a tertiary base at a pH of 6.5 to 10 at 50 ° C. up to the reflux temperature to give the corresponding thiazoline of the formula (I), and processes for the preparation of (S)-α-methylcysteine hydrochloride and its use for the preparation of thiazolines of the formula (I).

  制备式(I)中取代噻唑环的过程，其中Ar是苯基、萘基、噻吩基、吡啶基或喹啉基，可选择地被一种或多种卤素、OH、苄氧基、C1-C4烷基、C1-C4烷氧基、COOR1（其中R1为H或C1-C4烷基）取代，通过(S)-α-甲基半胱氨酸盐酸盐（式II）与式（III）Ar—CN（其中Ar如上定义）或相应的C1-C4烷基亚胺酯偶联，在适当的溶剂中，在pH为6.5至10、50℃至沸腾温度下，在三级碱的存在下反应，得到相应的式(I)中的噻唑环，以及制备(S)-α-甲基半胱氨酸盐酸盐的过程和其用于制备式(I)中的噻唑环的过程。
• Substituent Effects on Desferrithiocin and Desferrithiocin Analogue Iron-Clearing and Toxicity Profiles
  作者：Raymond J. Bergeron、Jan Wiegand、Neelam Bharti、James S. McManis

  DOI：10.1021/jm300509y

  日期：2012.8.23

  Desferrithiocin (DFT, 1) is a very efficient iron chelator when given orally. However, it is severely nephrotoxic. Structure-activity studies with 1 demonstrated that removal of the aromatic nitrogen to provide desazadesferrithiocin (DADFT, 2) and introduction of either a hydroxyl group or a polyether fragment onto the aromatic ring resulted in orally active iron chelators that were much less toxic than 1. The purpose of the current study was to determine if a comparable reduction in renal toxicity could be achieved by performing the same structural manipulations on 1 itself. Accordingly, three DFT analogues were synthesized. The iron-clearing efficiency and ferrokinetics were evaluated in rats and primates; toxicity assessments were carried out in rodents. The resulting DFT ligands demonstrated a reduction in toxicity that was equivalent to that of the DADFT analogues and presented with excellent iron-clearing properties.
• Bisebromoamide, a Potent Cytotoxic Peptide from the Marine Cyanobacterium <i>Lyngbya</i> sp.: Isolation, Stereostructure, and Biological Activity
  作者：Toshiaki Teruya、Hiroaki Sasaki、Hidesuke Fukazawa、Kiyotake Suenaga

  DOI：10.1021/ol9020546

  日期：2009.11.5

  A novel cytotoxic peptide, termed bisebromoamide (1), has been isolated from the marine cyanobacterium Lyngbya sp. Its planar structure was determined by 1D and 2D NMR spectroscopy. The absolute stereostructure of 1 was determined by chemical degradation followed by chiral HPLC analysis. Bisebromoamide (1) exhibited potent protein kinase inhibition: the phosphorylation of ERK in NRK cells by PDGF-stimulation was selectively inhibited by treatment with 10-0.1 mu M of 1.