(S)-3-(<(tert-butoxy)carbonyl>amino)-7-(<(2-chlorobenzyloxy)carbonyl>amino)-1-diazoheptan-2-one | 210533-60-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-3-(<(tert-butoxy)carbonyl>amino)-7-(<(2-chlorobenzyloxy)carbonyl>amino)-1-diazoheptan-2-one
• 英文别名: 2-chlorobenzyl N-((5S)-5-{[(tert-butoxy)carbonyl]amino}-7-diazo-6-oxoheptyl)carbamate；tert-butyl N-[(3S)-7-[(2-chlorophenyl)methoxycarbonylamino]-1-diazo-2-oxoheptan-3-yl]carbamate
• CAS: 210533-60-1
• 化学式: C₂₀H₂₇ClN₄O₅
• 分子量: 438.911
• InChiKey: QMLXMHNUURIQRV-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  30
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  95.7
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-3-(<(tert-butoxy)carbonyl>amino)-7-(<(2-chlorobenzyloxy)carbonyl>amino)-1-diazoheptan-2-one 在 silver trifluoroacetate 水 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 H-β³-HThr(OBn)-β³-HLys(2-Cl-Z)-OMe
  参考文献：
  名称：

  Synthesis and Biological Evaluation of a Cyclo--tetrapeptide as a Somatostatin Analogue

  摘要：

  Short β-peptides can mimic natural peptide hormones, as has been shown with a cyclo-β-tetrapeptide (1) that displays micromolar affinity to human somatostatin receptors. β-Peptides are thus a promising new class of peptidomimetics with potential high bioavailability due to their excellent resistance against proteases.

  DOI：

  10.1002/(sici)1521-3773(19990503)38:9<1223::aid-anie1223>3.0.co;2-a
• 作为产物：
  描述：

  N-叔丁氧羰基-N'-(2-氯苄氧羰基)-L-赖氨酸 在 N-甲基吗啉 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.0h， 生成 (S)-3-(<(tert-butoxy)carbonyl>amino)-7-(<(2-chlorobenzyloxy)carbonyl>amino)-1-diazoheptan-2-one
  参考文献：
  名称：

  Direct synthesis of N-protected β-amino dimethylhydroxamates: Application to the solid-phase synthesis of a peptide incorporating a new amide bond surrogate Ψ[CH2CH2NH]

  摘要：

  A rapid and efficient one-step synthesis of N-protected beta-amino dimethylhydroxamates starting from diazo ketones is reported A Fmoc-protected beta-amino aldehyde obtained by reduction of its corresponding dimethylhydroxamate was incorporated during solid phase assembly of an antigenic peptide. The resulting pseudopeptide containing an ethylene amino bond Psi[CH2CH2NH] was efficiently recovered. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00675-3

文献信息

• The Cyclo-β-Tetrapeptide (β-HPhe-β-HThr-β-HLys-β-HTrp): Synthesis, NMR Structure in Methanol Solution, and Affinity for Human Somatostatin Receptors
  作者：Karl Gademann、Martin Ernst、Dieter Seebach、Daniel Hoyer

  DOI：10.1002/(sici)1522-2675(20000119)83:1<16::aid-hlca16>3.0.co;2-3

  日期：2000.1.19

  Z)-OMe. The (N-Me)-β-HThr-(N-Me)-β-HPhe analog was also prepd. C- and N-terminal deprotection and cyclization through the pentafluorophenyl ester gave the insol. beta-tetrapeptide with protected Thr and Lys side chains. Solubilization and debenzylation could only be effected in LiCl-contg. THF (ca. 10% yield; with ca. 55% recovery). HPLC Purifn. provided a sample of the title compd., the structure

  环（β-HAla）4 的已知固态结构用于模拟环-β-四肽（β-HPhe-β-HThr-β-HLys-β-HTrp）的结构，作为一种前瞻性的生长抑素模拟物。合成开始于 N-保护的天然氨基酸 Boc-Phe-OH、Boc-Trp-OH、Boc-Lys(2-Cl-Z)-OH (2-Cl-Z = o-chlorobenzyloxycarbonyl) 和 Boc- Thr(OBn)-OH (Bn = 苄基)，与相应的 β-氨基酸衍生物同源。并与 β-四肽 Boc-β-HTrp-β-HPhe-β-HThr(OBn)-β-HLys(2-Cl-Z)-OMe 偶联。还制备了 (N-Me)-β-HThr-(N-Me)-β-HPhe 类似物。通过五氟苯基酯的C-和N-末端去保护和环化得到insol。具有受保护的 Thr 和 Lys 侧链的 β-四肽。增溶和脱苄基只能在 LiCl-contg 中进行。THF（产率约
• (S)-β3-Homolysine- and (S)-β3-Homoserine-Containingβ-Peptides: CD Spectra in Aqueous Solution
  作者：Stefan Abele、Gilles Guichard、Dieter Seebach

  DOI：10.1002/(sici)1522-2675(19981216)81:12<2141::aid-hlca2141>3.0.co;2-5

  日期：1998.12.16

  For further structural studies and for physiological investigations of beta-peptides, it is necessary to have H2O-soluble derivatives. Thus, we have prepared beta-hexa-, beta-hepta-, and beta-nonapeptides (1-6) with two, three, and seven side chains of lysine and serine. To detect possible pi-pi interactions, we also included the beta-amino acid beta(2)-HHop, resulting from homologation of so-called homophenylalanine (Hop) (5 and 6). The Fmoc-beta(2)- and beta(3)-amino-acid derivatives (11-14 and 19), and the corresponding beta-peptides were prepared by methods previously described (solid-phase peptide coupling; HPLC-pure samples, Fig. I). Circular-dichroism spectra (Fig.2) indicate the presence of less pronounced secondary structures (especially of the lysine analogues with multiple positive charge) in H2O as compared to MeOH. The beta(3)-heptapeptide (3) with two serine side chains is well soluble in H2O and exhibits the CD pattern typical of the 3(1)-helical structure.