D-ornithine

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: D-ornithine
• 英文别名: (2R)-5-amino-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)pentanoic acid；(2R)-5-amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)pentanoic acid
• 化学式: C₂₀H₂₂N₂O₄
• 分子量: 354.406
• InChiKey: ASLOVDWQFVNFRC-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Fmoc-D-苯丙氨酸 、 D-ornithine 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.08h， 生成 D-F-D-O-D-F-D-O
  参考文献：
  名称：

  Antiplasmodial activity of short peptide-based compounds

  摘要：

  合成了三系列基于短肽的化合物，经评估对疟原虫Plasmodium falciparum的氯喹敏感（D6）和氯喹耐药（W2）菌株进行体外实验，产生的IC₅₀值范围在1.4-4.7 μg mL⁻¹之间。

  DOI：

  10.1039/c5ra00779h

文献信息

• Novel Ligands Lacking a Positive Charge for the δ- and μ-Opioid Receptors
  作者：Peter W. Schiller、Irena Berezowska、Thi M.-D. Nguyen、Ralf Schmidt、Carole Lemieux、Nga N. Chung、Margaret L. Falcone-Hindley、Wenqing Yao、Josephine Liu、Seiji Iwama、Amos B. Smith、Ralph Hirschmann

  DOI：10.1021/jm990461z

  日期：2000.2.1

  same libraries for ligands of the delta-opioid receptor, we identified four compounds (1-4) which represent a new class of delta-opioid antagonists, some of which were also NK-1 receptor antagonists. The most potent delta-opioid antagonist, c[-Pro-1-Nal-D-Trp-Tyr-Thr-Phe-] (2), showed a K(e) value of 128 nM in the mouse vas deferens assay and a delta-receptor binding affinity constant of 152 nM in the

  最近，我们报道了使用微型文库取代有效的生长抑素激动剂L-363,301（c [-Pro-Phe-D-Trp-Lys-Thr-Phe-]）的Lys（9）[生长抑素（SRIF）编号]以产生有效的神经激肽受体（NK-1）拮抗剂c [-Pro-Phe-D-Trp-pF-Phe-Thr-Phe-]。这种新的环状六肽不结合SRIF受体。因此，单个突变转化了L-363,301，一种具有约ca.10效力的SRIF激动剂。SRIF在实验动物中效力的2-8倍（24）在体外具有选择性IC-1（50）为2 nM的选择性NK-1受体拮抗剂。在针对δ阿片受体配体的相同文库的筛选过程中，我们鉴定了代表新一类δ阿片拮抗剂的四种化合物（1-4），其中一些也是NK-1受体拮抗剂。最有效的δ阿片类药物拮抗剂c [-Pro-1-Nal-D-Trp-Tyr-Thr-Phe-]（2），在小鼠输精管试验中显示的K（e）值为128 nM
• Structure-activity relationship studies on the inhibition of the bacterial translation of novel Odilorhabdins analogues
  作者：Einars Loza、Matthieu Sarciaux、Martins Ikaunieks、Martins Katkevics、Tatyana Kukosha、Nadezhda Trufilkina、Victoria Ryabova、Kirill Shubin、Lucile Pantel、Marine Serri、Douglas L Huseby、Sha Cao、Kavita Yadav、Karin Hjort、Diarmaid Hughes、Maxime Gualtieri、Edgars Suna、Emilie Racine

  DOI：10.1016/j.bmc.2020.115469

  日期：2020.6

  A structure-activity relationship (SAR) study of NOSO-95179, a nonapeptide from the Odilorhabdin class of antibacterials, was performed by systematic variations of amino acids in positions 2 and 5 of the peptide. A series of non-proteinogenic amino acids was synthesized in high enantiomeric purity from Williams' chiral diphenyloxazinone by highly diastereoselective alkylation or by aldol-type reaction

  通过对肽第2位和第5位的氨基酸进行系统性变异，对NOSO-95179（一种来自Odilorhabdin类抗菌剂的九肽）进行了结构活性关系（SAR）研究。通过高度非对映选择性烷基化或醛醇型反应，从威廉姆斯的手性二苯基恶嗪酮合成了一系列非对映体高纯度氨基酸。使用固相肽合成方法制备了用于SAR研究的NOSO-95179类似物。使用体外测试来测量每种合成的奥地洛滨类似物对细菌翻译的抑制作用。对于最有效的类似物，测定了对两种野生型肠杆菌科细菌（大肠杆菌和肺炎克雷伯菌）的抗菌效果以及对流出缺陷型大肠杆菌的抗菌效果。
• Synthetic strategy for side chain mono-N-alkylation of Fmoc-amino acids promoted by molecular sieves
  作者：Luca Monfregola、Stefania De Luca

  DOI：10.1007/s00726-010-0798-6

  日期：2011.10

  A new synthetic strategy to alkylate amino groups under mild conditions has been developed. It utilizes only 4 angstrom molecular sieves as base in order to promote the N-alkylation reaction, in presence of the appropriate alkyl halide. The methodology was validated by the simple and efficient side-chain N-alkylation of o-Ns-protected Fmoc-amino acid. One of them was introduced as building block into a peptide sequence, thus allowing the preparation of site-specific alkylated peptide molecules.
• Cyclic Peptides As C5a Receptor Antagonists
  申请人：Pfizer Inc.

  公开号：US20190270778A1

  公开（公告）日：2019-09-05

  The invention relates to cyclic peptide derivatives, to their use in medicine, to compositions containing them, to processes for their preparation and to intermediates used in such processes. More particularly the invention relates to cyclic peptide C5a receptor antagonists of formula (Ia) or formula (Ib), or pharmaceutically acceptable salts thereof, wherein R 1a , R 1b , R 2 , R 3 and R 4 areas defined in the description. C5a receptor antagonists are potentially useful in the treatment of a wide range of 1 disorders, including inflammatory disorders and immune disorders.
• Antiplasmodial activity of short peptide-based compounds
  作者：Amit Mahindra、Rahul P. Gangwal、Sunil Bansal、Nathan E. Goldfarb、Ben M. Dunn、Abhay T. Sangamwar、Rahul Jain

  DOI：10.1039/c5ra00779h

  日期：——

  Three series of short peptide-based compounds were synthesized, which upon evaluation against chloroquine-sensitive (D6) and chloroquine-resistant (W2) strains ofPlasmodium falciparum in vitro, produced IC₅₀values ranging between 1.4–4.7 μg mL⁻¹.

  合成了三系列基于短肽的化合物，经评估对疟原虫Plasmodium falciparum的氯喹敏感（D6）和氯喹耐药（W2）菌株进行体外实验，产生的IC₅₀值范围在1.4-4.7 μg mL⁻¹之间。