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Cyclic B-Tetra- and...
Cyclic B-Tetra- and Pentapeptides: Synthesis through On-Resin Cyclization and Confomrational Studies by X-Ray, NMR and CD Spectroscopy and Theoretical Calculations
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- Buttner, Frank (författare)
- Uppsala universitet,Kemiska institutionen,Organisk kemi I,avd för organisk kemi
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- Norgren, Anna (författare)
- Uppsala universitet,Kemiska institutionen,Organisk kemi I,avd för organisk kemi
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Zhang, Suode (författare)
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Prabpai, Samran (författare)
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Kongsaeree, Palangpon (författare)
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- Arvidsson, Per (författare)
- Uppsala universitet,Kemiska institutionen,Organisk kemi I,avd för organisk kemi
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(creator_code:org_t)
- Wiley, 2005
- 2005
- Engelska.
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Ingår i: Chem. Eur. J.. - : Wiley. ; 11, s. 6145-6158
- Relaterad länk:
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https://urn.kb.se/re...
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https://doi.org/10.1...
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Abstract
Ämnesord
Stäng
- The solution-phase synthesis of the simplest cyclic B-tetrapeptide, cyclo(B-Ala)4 (4), as well as the solidphase syntheses through side chain anchoring and on-resin cyclization of the cyclic B3-tetrapeptide cyclo-(B3hPhe-B3hLeu-B3hLys-B3hGln-) (14) and the first cyclic B3-pentapeptide cyclo- (B3hVal-B3hPhe-B3Leu- B3hLys-B3hLys-) (19) are reported. Extensive computational as well as spectroscopic studies, including X-ray and NMR spectroscopy, were undertaken to determine the preferred conformations of these unnatural oligomers in solution and in the solid state. cyclo(B-Ala)4 (4) with no chiral side chains is shown to exist as a mixture of rapidly interchanging conformers in solution, whereas inclusion of chiral side chains in the cyclo-B3-tetrapetpride causes stabilizaton of one dominating conformer. The cyclic B3-pentapeptide on the other hand shows larger conformational freedom. The X-ray structure of achiral cyclo(B-Ala)4 (4) displays a Ci-symmetrical 16-membered ring with adjacent C=O and N-H atoms pointing pair wise up and down with respect to the ring plane. CD spectorscopic examinations of all cyclic B-peptides were undertaken and revealed results valuable as starting point for further structural investigations of these entities.
Ämnesord
- NATURVETENSKAP -- Kemi -- Organisk kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences -- Organic Chemistry (hsv//eng)
Nyckelord
- conformation analysis
- cyclization
- NMR spectroscopy
- peptides
- Organic chemistry
- Organisk kemi
Publikations- och innehållstyp
- ref (ämneskategori)
- art (ämneskategori)
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