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Synthesis and confo...
Synthesis and conformational studies of a β-turn mimetic incorporated in Leu-enkephalin
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- Blomberg, David (författare)
- Umeå universitet,Kemiska institutionen
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- Hedenström, Mattias (författare)
- Umeå universitet,Kemiska institutionen
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- Kreye, Paul (författare)
- Umeå universitet,Kemiska institutionen
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- Sethson, Ingmar (författare)
- Umeå universitet,Kemiska institutionen
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- Brickmann, Kay (författare)
- AstraZeneca R&D Mölndal, Mölndal, Sweden
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- Kihlberg, Jan (författare)
- Umeå universitet,Kemiska institutionen,AstraZeneca R&D Mölndal, Mölndal, Sweden
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(creator_code:org_t)
- 2004-04-20
- 2004
- Engelska.
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Ingår i: Journal of Organic Chemistry. - : American Chemical Society (ACS). - 0022-3263 .- 1520-6904. ; 69:10, s. 3500-3508
- Relaterad länk:
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https://urn.kb.se/re...
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visa fler...
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https://doi.org/10.1...
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Abstract
Ämnesord
Stäng
- A β-turn mimetic in which the four amino acids of a β-turn have been replaced by a 10-membered ring has been designed, synthesized, and subjected to conformational studies. In the mimetic, the intramolecular COi − HNi+3 hydrogen bond that is often found in β-turns has been replaced by an ethylene bridge. In addition, the amide bond between residues i and i + 1 was exchanged for a methylene ether isoster. Such a β-turn mimetic, based on the first four residues of Leu-enkephalin (Tyr-Gly-Gly-Phe-Leu), was prepared in 15 steps. The synthesis relied on a β-azido alcohol prepared in five steps from Cbz-Tyr(tBu)-OH as a key, i-position building block. tert-Butyl bromoacetate, glycine, and a Phe-Leu dipetide were then used as building blocks for positions i + 1, i + 2, and i + 3, respectively. Conformational studies based on 1H NMR data showed that the β-turn mimetic was flexible, but that it resembled a type-II β-turn at low temperature. This low energy conformer closely resembled the structure determined for crystalline Leu-enkephalin.
Ämnesord
- NATURVETENSKAP -- Kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences (hsv//eng)
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- art (ämneskategori)
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