Self-Assembling, Cystine-Derived, Fused Nanotubes Based on Spirane Architecture: Design, Synthesis, and Crystal Structure of Cystinospiranes
| Autor: | Darshan Ranganathan, Manoj P. Samant, Isabella L. Karle |
|---|---|
| Rok vydání: | 2001 |
| Předmět: |
chemistry.chemical_classification
Nanotube Molecular Structure Hydrogen bond Chemistry Stacking Cystine Hydrogen Bonding General Chemistry Crystal structure Crystallography X-Ray Peptides Cyclic Biochemistry Protein Structure Secondary Catalysis Amino acid Ring size Crystallography chemistry.chemical_compound Colloid and Surface Chemistry Molecule Spiro Compounds Crystallization |
| Zdroj: | Journal of the American Chemical Society. 123:5619-5624 |
| ISSN: | 1520-5126 0002-7863 |
| Popis: | 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: C(33)H(52)N(4)O(16)S(4), space group C2, a = 42.181(3) A, b = 5.1165(7) A, c = 11.8687(9) A, beta = 106.23(1) degrees. |
| Databáze: | OpenAIRE |
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