HCl*H-Lys(COCF₃)-D-Ala-D-Ala-OMe | 1313490-36-6

• 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: HCl*H-Lys(COCF₃)-D-Ala-D-Ala-OMe
• 英文别名: H-Lys(Tfa)-D-Ala-D-Ala-OMe hydrochloride；HCl*H-L-Lys(COCF3)-D-Ala-D-Ala-OMe；H-Lys(Tfa)-D-Ala-D-Ala-OMe*HCl
• CAS: 1313490-36-6
• 化学式: C₁₅H₂₅F₃N₄O₅*ClH
• 分子量: 434.843
• InChiKey: AFHDXQUAMWOPCF-RIHXGJNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.23
• 重原子数：
  28.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  139.62
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  HCl*H-Lys(COCF₃)-D-Ala-D-Ala-OMe 在 盐酸 、 lithium hydroxide monohydrate 、 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 、 4-(4,6-二甲氧基三嗪-2-基)-4-甲基吗啉盐酸盐 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  N-Methylimidazolium chloride-catalyzed pyrophosphate formation: Application to the synthesis of Lipid I and NDP-sugar donors

  摘要：

  N-Methylimidazolium chloride is found to catalyze a coupling reaction between monophosphates and activated phosphorous-nitrogen intermediates such as a phosphorimidazolide and phosphoromorpholidate to form biologically important unsymmetrical pyrophosphate diesters. The catalyst is much more active, cheaper, and less explosive than 1H-tetrazole, known as the best catalyst for the pyrophosphate formation over a decade. The mild and neutral reaction conditions are compatible with allylic pyrophosphate formation in Lipid I syntheisis. (31)P NMR experiments suggest that the catalyst acts not only as an acid but also as a nucleophile to form cationic and electrophilic phosphor-N-methylimidazolide intermediates in the pyrophosphate formation. (c) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.061
• 作为产物：
  描述：

  Boc-Lys-(N^ε-COCF3)-(D)-Ala-(D)-Ala-OMe 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 HCl*H-Lys(COCF₃)-D-Ala-D-Ala-OMe
  参考文献：
  名称：

  用于合成脂质 II 类似物的一锅保护糖基化反应

  摘要：

  (2,6-二氯-4-甲氧基苯基)(2,4-二氯苯基)甲基三氯乙酰亚胺酯( 3 )及其聚合物支撑试剂4可成功应用于一锅保护糖基化反应，形成二糖衍生物7d 用于合成脂质 II 类似物。C-6位的临时保护基或连接基和7d的N -Troc保护基可以通过还原条件同时裂解。通过使用所描述的方法，脂质 II ( 1 ) 和橙花基脂质 II N ε -丹磺基硫脲的合成总产率显着提高。 

  DOI：

  10.1002/chem.201400307

文献信息

• A New Oxyma Derivative for Nonracemizable Amide-Forming Reactions in Water
  作者：Qinghui Wang、Yong Wang、Michio Kurosu

  DOI：10.1021/ol3013556

  日期：2012.7.6

  An Oxyma derivative, (2,2-dimethyl-1,3-dioxolan-4-yl)methyl 2-cyano-2-(hydroxyimino)acetate (2), displayed remarkable physicochemical properties as a peptide-coupling additive for peptide-forming reactions in water. Short peptides to oligopeptides could be synthesized by using 2, EDCI, and NaHCO3 in water without measurable racemization. Significantly, a simple basic and acidic aqueous workup procedure can remove all reagents utilized in the reactions to afford only coupling products in consistently excellent yields.
• Transpeptidase-Mediated Incorporation of <scp>d</scp>-Amino Acids into Bacterial Peptidoglycan
  作者：Tania J. Lupoli、Hirokazu Tsukamoto、Emma H. Doud、Tsung-Shing Andrew Wang、Suzanne Walker、Daniel Kahne

  DOI：10.1021/ja2040656

  日期：2011.7.20

  The beta-lactams are the most important class of antibiotics in clinical use. Their lethal targets are the transpeptidase domains of penicillin binding proteins (PBPs), which catalyze the cross-linking of bacterial peptidoglycan (PG) during cell wall synthesis. The transpeptidation reaction occurs in two steps, the first being formation of a covalent enzyme intermediate and the second involving attack of an amine on this intermediate. Here we use defined PG substrates to dissect the individual steps catalyzed by a purified E. coli transpeptidase. We demonstrate that this transpeptidase accepts a set of structurally diverse D-amino acid substrates and incorporates them into PG fragments. These results provide new information on donor and acceptor requirements as well as a mechanistic basis for previous observations that noncanonical D-amino acids can be introduced into the bacterial cell wall.