N-Boc-1-苯甲基-D-组氨酸 | 65717-64-8

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 组氨酸类衍生物
• 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: N-Boc-1-苯甲基-D-组氨酸
• 中文别名: N-叔丁氧羰基-1-苯甲基-D-组氨酸
• 英文名称: N-(t-butoxycarbonyl)-^im-benzyl-D-histidine
• 英文别名: Boc-D-His(Bzl)；(R)-3-(1-Benzyl-1H-imidazol-4-yl)-2-((tert-butoxycarbonyl)amino)propanoic acid；(2R)-3-(1-benzylimidazol-4-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 65717-64-8
• 化学式: C₁₈H₂₃N₃O₄
• 分子量: 345.398
• InChiKey: OUHPNBGKEMHUCQ-OAHLLOKOSA-N

物化性质

• 沸点：
  572.1±50.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  93.4
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2933290090

反应信息

• 作为反应物：
  描述：

  N-Boc-1-苯甲基-D-组氨酸 在 N-乙基吗啉 、 N-羟基丁二酰亚胺 、 1-羟基苯并三唑 、 苯甲醚 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 、 1-(4-氯苯基)-3-(4-甲基-1-哌嗪基)-2-丙炔-1-酮 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 PhO-CH2CO-D-His(Bzl)-D-Ala-OBzl
  参考文献：
  名称：

  Synthesis of D-Ala--D-Ala Analogues with Postulated Antibacterial Activity.

  摘要：

  The syntheses of the L,L- and D,D-stereoisomers of N-phenoxyacetyl-X-alanine in which X=His, Tyr, or Lys, are described. The antibacterial activity of some of the peptide derivatives and their synthetic intermediates have been examined. Some of the intermediates exhibited moderate activity against viridans streptococci, enterococci and Streptococcus agalactiae. None of the compounds were active against beta-lactamase producing bacteria or served as beta-lactamase inhibitors.

  DOI：

  10.3891/acta.chem.scand.38b-0647
• 作为产物：
  描述：

  S-Boc-2-巯基-4,6-二甲基嘧啶 、 N^im-benzyl-D-histidine 生成 N-Boc-1-苯甲基-D-组氨酸
  参考文献：
  名称：

  双肽段功能化的两亲物的聚集行为和对映选择性酯水解在其双层膜中

  摘要：

  合成了四种具有二肽片段的两亲物，其由一个组氨酰残基和另一个氨基酸残基组成，以及双链片段的二十六烷基部分（N+C5AlaHis2C16、N+C5LeuHis2C16、N+C5PheHis2C16 和 N+C5HisAla2C16）。它们的聚集体形态通过电子显微镜和差示扫描量热法表征。具有与二十六胺组分（N+C5AlaHis2C16、N+C5LeuHis2C16、N+C5PheHis2C16）结合的组氨酰残基的两亲物在水分散状态下形成多壁和单壁聚集体，而它们的超声处理溶液仅涉及单壁囊泡。另一方面，具有与二十六胺组分 (N+C5HisAla2C16) 结合的丙氨酰残基的两亲物在水分散体中提供管状聚集体。在单壁囊泡中进行的各种疏水性对映体酯的水解显示出相对较小的对映选择性。原因...

  DOI：

  10.1246/bcsj.58.172

文献信息

• New substituted thiophene carboxamides, process for their preparation and their use as medicaments
  申请人：Pfau Roland

  公开号：US20060293300A1

  公开（公告）日：2006-12-28

  The present invention relates to new substituted thiophene-2-carboxylic acid amides of general formula wherein A, and R 1 to R 8c are defined as in claim 1 , the tautomers, the enantiomers, the diastereomers, the mixtures thereof and the salts thereof, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases, which have valuable properties.

  本发明涉及一种新的通式为的取代噻吩-2-羧酸酰胺，其中A和R1至R8的定义如权利要求书所述，其互变异构体、对映异构体、顺反异构体、其混合物和其盐，特别是与无机或有机酸或碱的生理上可接受的盐，具有有价值的性质。
• <i>N</i>-Imidazolebenzyl-histidine Substitution in Somatostatin and in Its Octapeptide Analogue Modulates Receptor Selectivity and Function
  作者：Judit Erchegyi、Renzo Cescato、Beatrice Waser、Jean E. Rivier、Jean Claude Reubi

  DOI：10.1021/jm200307v

  日期：2011.9.8

  Despite 3 decades of focused chemical, biological, structural, and clinical developments, unusual properties of somatostatin (SRIF, 1) analogues are still being uncovered. Here we report the unexpected functional properties of 1 and the octapeptide cyclo(3-14)H-Cys-Phe-Phe-Trp(8)-Lys-Thr-Phe-Cys-OH (somatostatin numbering; OLT-8,9) substituted by imBzl-L- or -D-His at position 8. These analogues were tested for their binding affinity to the five human somatostatin receptors (sst(1-5)), as well as for their functional properties (or functionalities) in an sst(3) internalization assay and in an sst(3) luciferase reporter gene assay. While substitution of Trp(8) in somatostatin by imBzl-L-or-D-His(8) results in sst(3) selectivity, substitution of Trp(8) in the octapeptide 9 by imBzl-L-or-D-His(8) results in loss of binding affinity for sst(1,2,4,5) and a radical functional switch from agonist to antagonist.
• Syntheses of low-hemolytic antimicrobial gratisin peptides
  作者：Makoto Tamaki、Manabu Kokuno、Ichiro Sasaki、Yumiko Suzuki、Michiko Iwama、Kenichi Saegusa、Yusuke kikuchi、Mitsuno Shindo、Masahiro Kimura、Yoshiki Uchida

  DOI：10.1016/j.bmcl.2009.03.133

  日期：2009.5

  Antibiotic and hemolytic activities of gratisin (GR), cyclo(-Val(1)-Orn(2)-Leu(3)-D-Phe(4)-Pro(5)-D-Tyr(6)-)(2), and. fifteen GR analogues, which have various D-amino acid residues in place of D-Tyr(6,6') residues, were examined. Among them, [D-Orn(6,6')]-GR, [D-Lys(6,6')]-GR and [D-Arg(6,6')]-GR showed the strong activity against both Gram-positive and Gram-negative bacteria. In addition, the antibiotics showed significantly reduced toxicity against human blood cells compared with gramicidin S, cyclo(-Val(1)-Orn(2)-Leu(3)-D-Phe(4)-Pro(5)-)(2). (C) 2009 Elsevier Ltd. All rights reserved.
• US7732466B2
  申请人：——

  公开号：US7732466B2

  公开（公告）日：2010-06-08