(S)-3-<<(tert-butoxy)carbonyl>amino>-7-<<(2-chlorobenzyloxy)carbonyl>amino>heptanoic acid | 219967-67-6

• 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>heptanoic acid
• 英文别名: (3S)-3-{[(tert-butoxy)carbonyl]amino}-7-({[(2-chlorobenzyl)oxy]carbonyl}amino)heptanoic acid；Boc-β³-HLys(2-Cl-Z)-OH；Boc-β³-HLys(N^ε-2-Cl-Z)-OH；(3S)-7-[(2-chlorophenyl)methoxycarbonylamino]-3-[(2-methylpropan-2-yl)oxycarbonylamino]heptanoic acid
• CAS: 219967-67-6
• 化学式: C₂₀H₂₉ClN₂O₆
• 分子量: 428.913
• InChiKey: WENBZKKNXGEBCW-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  29
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  114
• 氢给体数：
  3
• 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>heptanoic acid 在 sodium hydroxide 、 二乙基异丙基胺 、 水 、 1,2-乙二硫醇 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 cyclo(β³-HTrp-β³-HPhe-β³-HThr(OBn)-β³-HLys(N^ε-2-Cl-Z))
  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：

  在 silver trifluoroacetate 水 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 (S)-3-<<(tert-butoxy)carbonyl>amino>-7-<<(2-chlorobenzyloxy)carbonyl>amino>heptanoic acid
  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

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
• Effective Preparation of <i>O</i>-Succinimidyl-2- (<i>tert</i>-butoxycarbonylamino)ethylcarbamate Derivatives from β-Amino Acids. Application to the Synthesis of Urea-Containing Pseudopeptides and Oligoureas
  作者：Gilles Guichard、Vincent Semetey、Claude Didierjean、André Aubry、Jean-Paul Briand、Marc Rodriguez

  DOI：10.1021/jo990092e

  日期：1999.11.1
• β- and γ-Di- and Tripeptides as Potential Substrates for the Oligopeptide Transporter hPepT1
  作者：Ina Hubatsch、Per I. Arvidsson、Dieter Seebach、Kristina Luthman、Per Artursson

  DOI：10.1021/jm070148u

  日期：2007.10.1

  The hPepT1-mediated transport properties of a series of 11 synthesized beta- and gamma-peptides have been studied in Caco-2 cells. The results show that several of the compounds interact with the peptide transporter, but only two beta-dipeptides act as substrates and are transported across the cell monolayers. These two are less-efficient substrates than alpha-peptides. Larger derivatives than beta-dipeptides do not act as hPepT1 substrates, but instead, they appear to be substrates for P-glycoprotein efflux.
• (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.
• β-Peptidic Secondary Structures Fortified and Enforced by Zn2+ Complexation – On the Way toβ-Peptidic Zinc Fingers?
  作者：Gérald Lelais、Dieter Seebach、Bernhard Jaun、Raveendra I. Mathad、Oliver Flögel、Francesco Rossi、Marino Campo、Arno Wortmann

  DOI：10.1002/hlca.339

  日期：2006.3

  The correlation between beta(2)-, beta(3)-, and beta(2,3)-amino acid-residue configuration and stability of helix and hairpin-turn secondary structures of peptides consisting of homologated proteinogenic amino acids is analyzed (Figs. 1-3). To test the power of Zn2+ ions in fortifying and/or enforcing secondary structures of beta-peptides, a beta-decapeptide, 1, four beta-octapeptides, 2-5, and a P-hexadecapeptide, 10, have been devised and synthesized. The design was such that the peptides would a) fold to a 14-helix (I and 3) or a hairpin turn (2 and 4), or form neither of these two secondary structures (i.e., 5), and b) carry the side chains of cysteine and histidine in positions, which will allow Zn2+ ions to use their extraordinary affinity for RS- and the imidazole N-atoms for stabilizing or destabilizing the intrinsic secondary structures of the peptides. Tlie beta-hexadecapeptide 10 was designed to a) fold to a turn, to which a 14-helical structure is attached through a P-dipeptide spacer, and b) contain two cysteine and two histidine side chains for Zn complexation, in order to possibly mimic a Zn-finger motif While CD spectra (Figs6-8 and 17) and ESI mass spectra (Figs. 9 and 18) are compatible with the expected effects of Zn 21 ions in all cases, it was shown by detailed NMR analyses of three of the peptides, i.e., 2, 3,5, in the absence and presence of ZnCl2, that i) beta-peptide 2 forms a hairpin turn in H2O, even without Zn complexation to the terminal beta(3)hHis and 3 hCys side chains (Fig. 11), ii) beta-peptide 3, which is present as a 14-helix in MeOH, is forced to a hairpin-turn structure by Zn complexation in H2O (Fig. 12), and iii) beta-peptide 5 is poorly ordered in CD3OH (Fig. 13) and in H2O (Fig. 14), with far-remote beta(3)hCys and beta(3)hHis residues, and has a distorted turn structure in the presence of Zn 21 ions in H2O, with proximate terminal Cys and His side chains.