H-Leu-Cys(1)-OMe.H-Leu-Cys(1)-OMe | 765897-68-5

• 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: H-Leu-Cys(1)-OMe.H-Leu-Cys(1)-OMe
• 英文别名: methyl (2R)-2-[[(2S)-2-amino-4-methylpentanoyl]amino]-3-[[(2R)-2-[[(2S)-2-amino-4-methylpentanoyl]amino]-3-methoxy-3-oxopropyl]disulfanyl]propanoate
• CAS: 765897-68-5
• 化学式: C₂₀H₃₈N₄O₆S₂
• 分子量: 494.677
• InChiKey: OLZTYSNEMFILCU-VGWMRTNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  32
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  213
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-{3-(3-氯-3-氧代丙氧基)-2,2-二[(3-氯-3-氧代丙氧基)甲基]丙氧基}丙酰氯 、 H-Leu-Cys(1)-OMe.H-Leu-Cys(1)-OMe 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以36%的产率得到
  参考文献：
  名称：

  Self-Assembling, Cystine-Derived, Fused Nanotubes Based on Spirane Architecture:  Design, Synthesis, and Crystal Structure of Cystinospiranes

  摘要：

  A novel family of cystine-based spirobicyclic peptides (cystinospiranes) has been synthesized by a single-step procedure involving condensation of pentaerythritol-derived tetrachloride with either the simple L-cystine dimethyl ester or its C,C'-extended bispeptides leading to a variety of 19-membered spirobicyclic peptides or its N,N'-extended bispeptides affording the ring-expanded 25-membered cystinospiranes. The design is flexible with respect to the ring size that can be adjusted depending upon the length of the N,N'-extended cystine bispeptide, and the choice of an amino acid, as illustrated here with the preparation of a large number of cystinospiranes containing a wide variety of amino acids. X-ray crystal structure of the parent spirane (5a) revealed nanotube formation by vertical stacking of relatively flat spirobicyclic molecules through contiguous NH- - -O=C hydrogen bonding. The fused pair of parallel nanotubes is open-ended, hollow, and extends to infinity. Crystallographic parameters are the following: C33H52N4O16S4, space group C2, a = 42.181(3) Angstrom, b = 5.1165(7) Angstrom, c = 11.8687(9) Angstrom, beta = 106.23(1)degrees.

  DOI：

  10.1021/ja0101734
• 作为产物：
  描述：

  胱氨酸二甲酯 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 H-Leu-Cys(1)-OMe.H-Leu-Cys(1)-OMe
  参考文献：
  名称：

  Cystinophanes，一个新的芳香族桥连胱氨酸环肽家族：合成、晶体结构、分子识别和构象研究

  摘要：

  一个新的芳香桥连胱氨酸环肽（胱氨酸）家族已通过一步法合成，包括 1,3 芳香族（Ph 或 Pyr 单元）二羰基二氯与简单的 l-胱氨酸二甲酯缩合，以提供胱氨酸26、39 和 52 元环分别通过 2+2、3+3 和 4+4 环化，或与胱氨酸双肽（H2N-Xaa-Cyst-Xaa-NH2）导致各种1+1 基于胱氨酸的肽环烷。1H NMR 和 CD 研究表明这些胱氨酸在溶液中采用β-转角结构。包含两个芳环的代表性成员 (3a) 的 X 射线晶体结构已显示塌陷的环构象，芳环的面对面取向几乎平行，核磁共振研究也表明了这一特征。Cysinocyclophanes 采用 β 转角型构象的倾向归因于 S-S 键的存在以及需要保持其扭转角的接近正交值。胱氨酸的潜力...

  DOI：

  10.1021/ja9734915

文献信息

• Cystinophanes, a Novel Family of Aromatic-Bridged Cystine Cyclic Peptides:  Synthesis, Crystal Structure, Molecular Recognition, and Conformational Studies
  作者：Darshan Ranganathan、V. Haridas、Isabella L. Karle

  DOI：10.1021/ja9734915

  日期：1998.4.1

  and CD studies have shown these cystinophanes to adopt a β-turn-like structure in solution. X-ray crystal structure of a representative member (3a) containing two aromatic rings has shown a collapsed ring conformation with a near parallel face-to-face orientation of aromatic ringsa feature also suggested by NMR studies. The propensity of cystinocyclophanes to adopt β-turn-type conformation is attributed

  一个新的芳香桥连胱氨酸环肽（胱氨酸）家族已通过一步法合成，包括 1,3 芳香族（Ph 或 Pyr 单元）二羰基二氯与简单的 l-胱氨酸二甲酯缩合，以提供胱氨酸26、39 和 52 元环分别通过 2+2、3+3 和 4+4 环化，或与胱氨酸双肽（H2N-Xaa-Cyst-Xaa-NH2）导致各种1+1 基于胱氨酸的肽环烷。1H NMR 和 CD 研究表明这些胱氨酸在溶液中采用β-转角结构。包含两个芳环的代表性成员 (3a) 的 X 射线晶体结构已显示塌陷的环构象，芳环的面对面取向几乎平行，核磁共振研究也表明了这一特征。Cysinocyclophanes 采用 β 转角型构象的倾向归因于 S-S 键的存在以及需要保持其扭转角的接近正交值。胱氨酸的潜力...
• Self-Assembling, Cystine-Derived, Fused Nanotubes Based on Spirane Architecture:  Design, Synthesis, and Crystal Structure of Cystinospiranes
  作者：Darshan Ranganathan、Manoj P. Samant、Isabella L. Karle

  DOI：10.1021/ja0101734

  日期：2001.6.1

  A novel family of cystine-based spirobicyclic peptides (cystinospiranes) has been synthesized by a single-step procedure involving condensation of pentaerythritol-derived tetrachloride with either the simple L-cystine dimethyl ester or its C,C'-extended bispeptides leading to a variety of 19-membered spirobicyclic peptides or its N,N'-extended bispeptides affording the ring-expanded 25-membered cystinospiranes. The design is flexible with respect to the ring size that can be adjusted depending upon the length of the N,N'-extended cystine bispeptide, and the choice of an amino acid, as illustrated here with the preparation of a large number of cystinospiranes containing a wide variety of amino acids. X-ray crystal structure of the parent spirane (5a) revealed nanotube formation by vertical stacking of relatively flat spirobicyclic molecules through contiguous NH- - -O=C hydrogen bonding. The fused pair of parallel nanotubes is open-ended, hollow, and extends to infinity. Crystallographic parameters are the following: C33H52N4O16S4, space group C2, a = 42.181(3) Angstrom, b = 5.1165(7) Angstrom, c = 11.8687(9) Angstrom, beta = 106.23(1)degrees.