BOC-L-Ala-L-Ala-OSu | 67818-94-4

• 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: BOC-L-Ala-L-Ala-OSu
• 英文别名: Boc-Ala-Ala-OSu；(2,5-dioxopyrrolidin-1-yl) (2S)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]propanoate
• CAS: 67818-94-4
• 化学式: C₁₅H₂₃N₃O₇
• 分子量: 357.364
• InChiKey: QTORJLMGKGYYIN-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.01
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  131.11
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  BOC-L-Ala-L-Ala-OSu 在 碳酸氢钠 、 苯甲醚 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 4.0h， 生成 L-Ala-L-Ala-DL-m-FPhe
  参考文献：
  名称：

  Transport of antimicrobial agents using peptide carrier systems: anticandidal activity of m-fluorophenylalanine-peptide conjugates

  摘要：

  A series of di- and tripeptides containing D- and L-m-fluorophenylalanine was prepared and tested in vitro for the ability to inhibit the growth of the yeast Candida albicans. The results demonstrate that peptides containing L-m-fluorophenylalanine inhibited the growth of C. albicans with minimum inhibitory concentrations (MIC's) ranging from 0.5 to 63 micrograms/mL. The parent L-m-fluorophenylalanine and peptides containing D-m-fluorophenylalanine were inactive (MIC greater than 250 micrograms/mL) in these tests. The results of competitive antagonism studies support peptide transport mediated entry of the inhibitory peptides, followed by release of L-m-fluorophenylalanine inside the cell.

  DOI：

  10.1021/jm00366a013

文献信息

• [EN] LEVORPHANOL PRODRUGS AND PROCESSES FOR MAKING AND USING THEM<br/>[FR] PROMÉDICAMENTS DE LEVORANOL ET LEURS PROCÉDÉS DE FABRICATION ET D'UTILISATION
  申请人：KEMPHARM INC

  公开号：WO2018191472A1

  公开（公告）日：2018-10-18

  The presently described technology provides compositions of one or more of oxoacids, polyethylene glycols, and vitamin compounds chemically conjugated to levorphanol ((-)-17-methylmorphinan-3-ol) to form novel prodrugs and compositions of levorphanol.

  目前描述的技术提供了一种或多种羟基酸、聚乙二醇和维生素化合物与左旋吗啡醇((-)-17-甲基吗啡-3-醇)在化学上结合形成新型前药和左旋吗啡的组合物。
• [EN] DEXTRORPHAN PRODRUGS AND PROCESSES FOR MAKING AND USING THEM<br/>[FR] PROMÉDICAMENTS DE DEXTRORPHANE ET LEURS PROCÉDÉS DE FABRICATION ET D'UTILISATION
  申请人：KEMPHARM INC

  公开号：WO2018191477A1

  公开（公告）日：2018-10-18

  The presently described technology provides compositions of one or more of oxoacids, polyethylene glycols, and/or vitamin compounds chemically conjugated to dextrorphan, (+)-17-methylmorphinan-3-ol), to form novel prodrugs and compositions of dextrorphan.

  目前描述的技术提供了将一种或多种羟基酸、聚乙二醇和/或维生素化学共轭到右旋丙啡醇（(+)-17-甲基吗啡酮-3-醇）上，形成新型前药和右旋丙啡醇组合物的配方。
• Synthesis and Antimicrobial and Toxicological Studies of Amino Acid and Peptide Derivatives of Kanamycin A and Netilmicin
  作者：S. Kotretsou、M. P. Mingeot-Leclercq、V. Constantinou-Kokotou、R. Brasseur、M. P. Georgiadis、P. M. Tulkens

  DOI：10.1021/jm00023a011

  日期：1995.11

  Amino acid and peptide derivatives of aminoglycosides have been obtained by substitution of the 1-N or 6'-N amino functions of kanamycin A and netilmicin via the temporary complexation of vicinal and nonvicinal amino and hydroxy functions by copper ion [1-N kanamycin A derivatives: L-Ala(Ga), D-Ala (6b), Gly (6c), L-Asp (6d), L-Ala-L-Ala (6e). 6'-N kanamycin A derivatives: L-Ala (3a), D-Ala (3b), Gly (3c), L-Ala-L-Ala (3e), L-Leu (3f). 6'-N netilmicin derivatives: L-Ala(9a), D-Ala (9b), Gly (9c), L-Asp (9d), L-Ala-L-Ala (9e)]. Characterization was made by FAB-MS, IR, H-1-NMR, and C-13-NMR. All derivatives were essentially inactive. The nephrotoxic potential of the derivatives obtained in sufficient quantities (3b,e and 9a-e) was assessed by measuring their inhibitory potential toward the activity of lysosomal phospholipase A(1) acting on phosphatidylcholine embedded in negatively-charged membranes. One compound, 6'-N-L-Ala-netilmicin (9a), showed a a-fold decrease of inhibitory potency compared to its parent drug. A conformational analysis revealed that it adopts two equally probable conformations and orientations when interacting with phosphatidylinositol. The first in which the drug lies parallel to the hydrophobic-hydrophilic interface, is similar to that of netilmicin. The second, in which the drug inserts itself in the bilayer across the hydrophilic/hydrophobic interface, is similar to that described for streptomycin, an almost non-nephrotoxic aminoglycoside.
• Influencing Antibody-Mediated Attenuation of Methamphetamine CNS Distribution through Vaccine Linker Design
  作者：Major Gooyit、Pedro O. Miranda、Cody J. Wenthur、Alex Ducime、Kim D. Janda

  DOI：10.1021/acschemneuro.6b00389

  日期：2017.3.15

  Active vaccination examining a single hapten engendered with a series of peptidic linkers has resulted in the production of antimethamphetamine antibodies. Given the limited chemical complexity of methamphetamine, the structure of the linker species embedded within the hapten could have a substantial effect on the ultimate efficacy of the resulting vaccines. Herein, we investigate linker effects by generating a series of methamphetamine haptens that harbor a linker with varying amino acid identity, peptide length, and associated carrier protein. Independent changes in each of these parameters were found to result in alterations in both the quantity and quality of the antibodies induced by vaccination. Although it was found that the consequence of the linker design was also dependent on the identity of the carrier protein, we demonstrate overall that the inclusion of a short, structurally simple, amino acid linker benefits the efficacy of a methamphetamine vaccine in limiting brain penetration of the free drug.
• Transport of antimicrobial agents using peptide carrier systems: anticandidal activity of m-fluorophenylalanine-peptide conjugates
  作者：William D. Kingsbury、Jeffrey C. Boehm、Rajanikant J. Mehta、Sarah F. Grappel

  DOI：10.1021/jm00366a013

  日期：1983.12

  A series of di- and tripeptides containing D- and L-m-fluorophenylalanine was prepared and tested in vitro for the ability to inhibit the growth of the yeast Candida albicans. The results demonstrate that peptides containing L-m-fluorophenylalanine inhibited the growth of C. albicans with minimum inhibitory concentrations (MIC's) ranging from 0.5 to 63 micrograms/mL. The parent L-m-fluorophenylalanine and peptides containing D-m-fluorophenylalanine were inactive (MIC greater than 250 micrograms/mL) in these tests. The results of competitive antagonism studies support peptide transport mediated entry of the inhibitory peptides, followed by release of L-m-fluorophenylalanine inside the cell.