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Carbohydrate amino acids: the intrinsic conformational preference for a beta-turn-type structure in a carbopeptoid building block.

Abstract:

Infrared ion-dip spectroscopy coupled with DFT and ab initio calculations are used to establish the intrinsic conformational preference of the basic structural unit of a peptide mimic, a cis-tetrahydrofuran-based "carbopeptoid" (amide-sugar-amide), isolated at low temperature in the gas phase. The carbopeptoid units form a beta-turn-type structure, stabilized by an intramolecular NH --> O=C hydrogen bond across the sugar ring, thus forming a 10-membered, C10 turn. Despite the clear prefere...

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Publication status:
Published

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Publisher copy:
10.1021/ja0607133

Authors


Jockusch, RA More by this author
Talbot, FO More by this author
Rogers, PS More by this author
Simone, MI More by this author
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Journal:
Journal of the American Chemical Society
Volume:
128
Issue:
51
Pages:
16771-16777
Publication date:
2006-12-05
DOI:
EISSN:
1520-5126
ISSN:
0002-7863
URN:
uuid:82152f70-c588-41e4-ad34-769efe397280
Source identifiers:
40179
Local pid:
pubs:40179

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