(3S,4S)-4-[(芴甲氧羰基)氨基]-3-羟基-6-甲基庚酸 | 158257-40-0

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - FMOC-氨基酸
• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: (3S,4S)-4-[(芴甲氧羰基)氨基]-3-羟基-6-甲基庚酸
• 英文名称: Fmoc-3S,4S-Sta-OH
• 英文别名: Fmoc-Sta-OH；(3S,4S)-4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-hydroxy-6-methylheptanoic acid；(3S,4S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-6-methylheptanoic acid
• CAS: 158257-40-0
• 化学式: C₂₃H₂₇NO₅
• mdl: MFCD0006567
• 分子量: 397.471
• InChiKey: JGUYYODGVQXZAY-SFTDATJTSA-N

物化性质

• 熔点：
  92-94°C
• 沸点：
  628.2±55.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.391
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• WGK Germany：
  2
• 海关编码：
  29225090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  -20°C

反应信息

• 作为反应物：
  描述：

  (3S,4S)-4-[(芴甲氧羰基)氨基]-3-羟基-6-甲基庚酸 在 porcine liver esterase 、 N-羟基-7-氮杂苯并三氮唑 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 水 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.08h， 生成 acetyl-Leu-(3S,4S)-4-amino-3-hydroxy-6-methylheptanoyl-(S)-α-aminobutyryl-4-amino-7-guanidino-hept-2-enoic acid
  参考文献：
  名称：

  Total synthesis of miraziridine A and identification of its major reaction site for cathepsin B

  摘要：

  The synthesis of miraziridine A, a pentapeptide derivative isolated from marine sponge, and its truncated analogs has been achieved. To construct the backbone of miraziridine A, a side-chain-unprotected vinylogous arginine was condensed with an aziridine-containing fragment prepared by a conventional solid-phase procedure. An analog lacking the vinylogous arginine site showed comparable inhibitory activity with miraziridine A, whereas an analog lacking the aziridine site showed remarkably weak inhibitory activity for cathepsin B. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.082
• 作为产物：
  描述：

  Boc-(3R,4S)-statine ethyl ester 在 lithium hydroxide 、 甲基磺酰氯 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.75h， 生成 (3S,4S)-4-[(芴甲氧羰基)氨基]-3-羟基-6-甲基庚酸
  参考文献：
  名称：

  Total synthesis of miraziridine A and identification of its major reaction site for cathepsin B

  摘要：

  The synthesis of miraziridine A, a pentapeptide derivative isolated from marine sponge, and its truncated analogs has been achieved. To construct the backbone of miraziridine A, a side-chain-unprotected vinylogous arginine was condensed with an aziridine-containing fragment prepared by a conventional solid-phase procedure. An analog lacking the vinylogous arginine site showed comparable inhibitory activity with miraziridine A, whereas an analog lacking the aziridine site showed remarkably weak inhibitory activity for cathepsin B. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.06.082

文献信息

• A New, Second Generation Trithiol Bifunctional Chelate for ^72,77As: Trithiol(b)-(Ser)₂-RM2
  作者：Firouzeh Najafi Khosroshahi、Yutian Feng、Li Ma、Simon Manring、Tammy L. Rold、Fabio A. Gallazzi、Steven P. Kelley、Mary F. Embree、Heather M. Hennkens、Timothy J. Hoffman、Silvia S. Jurisson

  DOI：10.1021/acs.bioconjchem.0c00658

  日期：2021.7.21

  Trithiol chelates are suitable for labeling radioarsenic (72As: 2.49 MeV β+, 26 h; 77As: 0.683 MeV β–, 38.8 h) to form potential theranostic radiopharmaceuticals for positron emission tomography (PET) imaging and therapy. A trithiol(b)-(Ser)2-RM2 bioconjugate and its arsenic complex were synthesized and characterized. The trithiol(b)-(Ser)2-RM2 bioconjugate was radiolabeled with no-carrier-added 77As in over 95% radiochemical yield and was stable for over 48 h, and in vitro IC50 cell binding studies of [77As]As-trithiol(b)-(Ser)2-RM2 in PC-3 cells demonstrated high affinity for the gastrin-releasing peptide (GRP) receptor (low nanomolar range). Limited biodistribution studies in normal mice were performed with HPLC purified 77As-trithiol(b)-(Ser)2-RM2 demonstrating both pancreatic uptake and hepatobiliary clearance.

  三硫醇配合物适用于标记放射性砷（72As：β+ 2.49 MeV，26小时；77As：β– 0.683 MeV，38.8小时），形成潜在的正电子发射断层扫描（PET）成像和治疗用放射性药物。合成并表征了一种三硫醇(b)-(Ser)2-RM2生物偶联物及其砷配合物。该生物偶联物在无载体添加的77As标记下，放射化学产率超过95%，稳定性超过48小时，并且[77As]As-三硫醇(b)-(Ser)2-RM2在PC-3细胞中的体外IC50细胞结合研究表明，对胃泌素释放肽（GRP）受体具有高亲和力（低纳摩尔范围）。在正常小鼠中进行了有限生物分布研究，通过HPLC纯化的77As-三硫醇(b)-(Ser)2-RM2显示胰腺摄取和肝胆清除。
• Synthesis and biochemical characterisation of fluorinated analogues of pepstatin A and grassystatin A
  作者：Aggie Lawer、John Nesvaderani、Gabriella M. Marcolin、Luke Hunter

  DOI：10.1016/j.tet.2017.12.033

  日期：2018.3

  statine-containing peptides that act as inhibitors of aspartic protease enzymes. In this work, stereoselective fluorination is investigated as a strategy for enhancing the pharmacodynamic and pharmacokinetic properties of these lead compounds. Fluorination is found to modestly affect the protease inhibitory potency, leading to the identification of two highly active new inhibitors of the cancer-associated

  Pepstatin A和Grassystatin A是天然的，含他汀类的肽，可作为天冬氨酸蛋白酶的抑制剂。在这项工作中，研究了立体选择性氟化作为增强这些先导化合物的药效和药代动力学性质的策略。发现氟化作用对蛋白酶的抑制能力有中等程度的影响，从而导致鉴定出两种与癌症相关的蛋白酶的高活性新抑制剂组织蛋白酶D。但是，在靶标选择性，亲脂性，膜通透性或代谢方面未观察到显着变化。稳定。
• Synthesis of chiral urethane N-alkoxycarbonyl tetramic acids from urethane N-carboxyanhydrides (UNCAs)
  作者：Jean-Alain Fehrentz、Elisabeth Bourdel、Jean-Christophe Califano、Olivier Chaloin、Chantal Devin、Patrick Garrouste、Ana-Christina Lima-Leite、Muriel Llinares、François Rieunier、Jean Vizavonna、François Winternitz、Albert Loffet、Jean Martinez

  DOI：10.1016/s0040-4039(00)76757-8

  日期：1994.3

  The synthesis of chiral N-protected tetramic acid derivatives which are important precursors of β-hydroxy γ-amino acid under mild conditions is described. Reaction of urethane-N-carboxyanhydrides (UNCAs) with Meldrum's acid in the presence of a tertiary amine, followed by subsequent cyclisation produced tetramic acid derivatives. This procedure is applicable to Boc-, Fmoc- and Z- N-carboxyanhydrides

  描述了在温和条件下手性N-保护的四酸衍生物的合成，该衍生物是β-羟基γ-氨基酸的重要前体。在叔胺存在下，氨基甲酸酯-N-羧基酐（UNCA）与Meldrum酸反应，然后环化生成四甲酸衍生物。此程序适用于Boc-，Fmoc-和Z- N-羧基酸酐。
• Methods for identifying compounds of interest using encoded libraries
  申请人：Praecis Pharmaceuticals Inc.

  公开号：EP2368868A1

  公开（公告）日：2011-09-28

  The present invention provides a method for identifying a compound of interest by screening libraries of molecules which include an encoding oligonucleotide tag.

  本发明提供了一种通过筛选包含编码寡核苷酸标记的分子库来识别感兴趣化合物的方法。
• Pepstatin A derivatives
  申请人：Freie Universität Berlin

  公开号：EP2113510A1

  公开（公告）日：2009-11-04

  The invention relates to a compound having a structure according to the general formula P3-P2-P1-P1'-P2' (I), wherein residues P3, P2, P1, P1' and P2' are specifically defined and may be, e. g., certain amino acid residues. The invention further relates to the use of said compound and to a method for synthesizing a peptide.

  本发明涉及一种具有结构通式P3-P2-P1-P1'-P2'（I）的化合物，其中残基P3，P2，P1，P1'和P2'具有特定定义，并且可以是某些氨基酸残基。本发明还涉及所述化合物的用途以及合成肽的方法。