期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 123, 期 24, 页码 5619-5624出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja0101734
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资金
- PHS HHS [30902] Funding Source: Medline
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.
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