Relevant bibliographies by topics / Γ-turn mimetics

Contents

  1. Journal articles
  2. Dissertations / Theses
  3. Book chapters

Academic literature on the topic 'Γ-turn mimetics'

Author: Grafiati
Published: 4 June 2021
Last updated: 1 February 2022

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Journal articles on the topic "Γ-turn mimetics"

1

Ferguson, Mark D., Joseph P. Meara, Hiroshi Nakanishi, Min S. Lee, and Michael Kahn. "The development of hydrazide γ-turn mimetics." Tetrahedron Letters 38, no. 40 (October 1997): 6961–64. http://dx.doi.org/10.1016/s0040-4039(97)01664-x.

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Lindvall, Mika K., Kari Rissanen, Juha M. L. Hakala, and Ari M. P. Koskinen. "Novel γ-turn mimetics with a reinforced hydrogen bond." Tetrahedron Letters 40, no. 41 (October 1999): 7427–30. http://dx.doi.org/10.1016/s0040-4039(99)01519-1.

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FERGUSON, M. D., J. P. MEARA, H. NAKANISHI, M. S. LEE, and M. KAHN. "ChemInform Abstract: The Development of Hydrazide γ-Turn Mimetics." ChemInform 29, no. 2 (June 24, 2010): no. http://dx.doi.org/10.1002/chin.199802207.

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Reetz, Manfred T., Nils Griebenow, and Richard Goddard. "Stereoselective syntheses of α-hydroxy-γ-amino acids: possible γ-turn mimetics." J. Chem. Soc., Chem. Commun., no. 16 (1995): 1605–6. http://dx.doi.org/10.1039/c39950001605.

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REETZ, M. T., N. GRIEBENOW, and R. GODDARD. "ChemInform Abstract: Stereoselective Syntheses of α-Hydroxy-γ-amino Acids: Possible γ-Turn Mimetics." ChemInform 27, no. 1 (August 12, 2010): no. http://dx.doi.org/10.1002/chin.199601225.

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Callahan, James F., Kenneth A. Newlander, Joelle L. Burgess, Drake S. Eggleston, Andrew Nichols, Angela Wong, and William F. Huffman. "The use of γ-turn mimetics to define peptide secondary structure." Tetrahedron 49, no. 17 (March 1993): 3479–88. http://dx.doi.org/10.1016/s0040-4020(01)90208-x.

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Lindvall, Mika K., Kari Rissanen, Juha M. L. Hakala, and Ari M. P. Koskinen. "ChemInform Abstract: Novel γ-Turn Mimetics with a Reinforced Hydrogen Bond." ChemInform 31, no. 2 (June 11, 2010): no. http://dx.doi.org/10.1002/chin.200002160.

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Schmidt, Boris. "Racemic, Yet Diastereomerically Pure Azido Acids as Both γ-Turn and Inverse γ-Turn Mimetics for Solid-Phase Peptide Synthesis." Synlett 1998, no. 11 (November 1998): 1240–42. http://dx.doi.org/10.1055/s-1998-3143.

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Baek, Bong-hyeon, Myung-ryul Lee, Kwang-Yon Kim, Ung-In Cho, Doo Wan Boo, and Injae Shin. "Novel Consecutive β- and γ-Turn Mimetics Composed of α-Aminooxy Tripeptides." Organic Letters 5, no. 7 (April 2003): 971–74. http://dx.doi.org/10.1021/ol020233q.

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Sato, M., Jessie Y. H. Lee, Hiroshi Nakanishi, Michael E. Johnson, R. Alan Chrusciel, and Michael Kahn. "Design, synthesis and conformational analysis of γ-turn peptide mimetics of bradykinin." Biochemical and Biophysical Research Communications 187, no. 2 (September 1992): 999–1006. http://dx.doi.org/10.1016/0006-291x(92)91296-3.

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Dissertations / Theses on the topic "Γ-turn mimetics"

1

Rosenström, Ulrika. "Design and Synthesis of AT2 Receptor Selective Angiotensin II Analogues Encompassing β- and γ-Turn Mimetics." Doctoral thesis, Uppsala universitet, Institutionen för läkemedelskemi, 2004. http://urn.kb.se/resolve?urn=urn:nbn:se:uu:diva-4642.

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Important information on the bioactive conformation of biologically active peptides may be obtained by studies of rigid peptides or well-defined secondary structure mimetics incorporated into pseudopeptides. The structural requirements for the interaction of angiotensin II (Ang II, Asp-Arg-Val-Tyr-Ile-His-Pro-Phe) with its AT1 and AT2 receptors were the subject of this study. The main objectives of this work were to synthesize secondary structure mimetics and incorporate these into Ang II. Ang II has been suggested to adopt a turn conformation around Tyr4 when interacting with its AT1 receptor. Therefore, two γ- and one β-turn mimetic scaffolds based on the benzodiazepine structure were synthesized and decorated with side chains. The scaffolds replaced the turn region around Tyr4. Most of the pseudopeptides obtained after incorporation into Ang II exhibited high AT2/AT1 selectivity and nanomolar affinity to the AT2 receptor. One pseudopeptide encompassing a β-turn mimetic also displayed AT1 receptor affinity. We hypothesized that the position of the guanidino group of the arginine residue and the N-terminal end, in relation to the tyrosine side chain, was critical for AT2 receptor affinity. Conformational evaluation of the pseudopeptides revealed that in all the compounds with AT2 receptor affinity the arginine side chain and the N-terminal end could reach common regions, not accessible to the inactive compound. It is proposed that Ang II has a more extended bioactive conformation when binding to the AT2 receptor than when binding to the AT1 receptor. Furthermore, in a Gly scan of Ang II only replacement of the arginine residue reduced the affinity for the AT2 receptor considerably. Some N-terminal modified Ang II analogues were also synthesized and it was concluded that truncated Ang II analogues interact with the AT2 receptor differently than Ang II. Three of the synthesized pseudopeptides were evaluated in AT2 receptor functional assays and were found to act as agonists.
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2

Rosenström, Ulrika. "Design and Synthesis of AT2 Receptor Selective Angiotensin II Analogues Encompassing β- and γ-Turn Mimetics." Doctoral thesis, Uppsala University, Department of Medicinal Chemistry, 2004. http://urn.kb.se/resolve?urn=urn:nbn:se:uu:diva-4642.

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Important information on the bioactive conformation of biologically active peptides may be obtained by studies of rigid peptides or well-defined secondary structure mimetics incorporated into pseudopeptides. The structural requirements for the interaction of angiotensin II (Ang II, Asp-Arg-Val-Tyr-Ile-His-Pro-Phe) with its AT1 and AT2 receptors were the subject of this study.

The main objectives of this work were to synthesize secondary structure mimetics and incorporate these into Ang II. Ang II has been suggested to adopt a turn conformation around Tyr4 when interacting with its AT1 receptor. Therefore, two γ- and one β-turn mimetic scaffolds based on the benzodiazepine structure were synthesized and decorated with side chains. The scaffolds replaced the turn region around Tyr4. Most of the pseudopeptides obtained after incorporation into Ang II exhibited high AT2/AT1 selectivity and nanomolar affinity to the AT2 receptor. One pseudopeptide encompassing a β-turn mimetic also displayed AT1 receptor affinity.

We hypothesized that the position of the guanidino group of the arginine residue and the N-terminal end, in relation to the tyrosine side chain, was critical for AT2 receptor affinity. Conformational evaluation of the pseudopeptides revealed that in all the compounds with AT2 receptor affinity the arginine side chain and the N-terminal end could reach common regions, not accessible to the inactive compound. It is proposed that Ang II has a more extended bioactive conformation when binding to the AT2 receptor than when binding to the AT1 receptor.

Furthermore, in a Gly scan of Ang II only replacement of the arginine residue reduced the affinity for the AT2 receptor considerably. Some N-terminal modified Ang II analogues were also synthesized and it was concluded that truncated Ang II analogues interact with the AT2 receptor differently than Ang II.

Three of the synthesized pseudopeptides were evaluated in AT2 receptor functional assays and were found to act as agonists.

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3

Georgsson, Jennie. "Design and Synthesis of Novel AT2 Receptor Ligands : From Peptides to Drug-Like Molecules." Doctoral thesis, Uppsala : Acta Universitatis Upsaliensis, 2006. http://urn.kb.se/resolve?urn=urn:nbn:se:uu:diva-6269.

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Andersson, Hanna. "Design and Synthesis of Angiotensin IV Peptidomimetics Targeting the Insulin-Regulated Aminopeptidase (IRAP)." Doctoral thesis, Uppsala : Acta Universitatis Upsaliensis, 2010. http://urn.kb.se/resolve?urn=urn:nbn:se:uu:diva-122218.

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Book chapters on the topic "Γ-turn mimetics"

1

Gu, Xuyuan, Wei Qiu, Jinfa Ying, John M. Ndungu, and Victor J. Hruby. "Synthesis of β-Turn Mimetics: [5,5]-Fused Bicyclic γ-Lactam Dipeptide Analogues." In Peptides: The Wave of the Future, 602–3. Dordrecht: Springer Netherlands, 2001. http://dx.doi.org/10.1007/978-94-010-0464-0_279.

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Deaudelin, Philippe, and William D. Lubell. "Synthesis of pyrrolo[3,2-e][1,4]diazepin-2-ones as potential γ-turn mimetics." In Advances in Experimental Medicine and Biology, 183–84. New York, NY: Springer New York, 2009. http://dx.doi.org/10.1007/978-0-387-73657-0_84.

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Newlander, Kenneth A., James F. Callahan, Michael L. Moore, Thaddeus A. Tomaszek, and William F. Huffman. "A novel constrained reduced-amide inhibitor of HIV-1 protease derived from the systematic incorporation of γ-turn mimetics into a model substrate." In Peptide Chemistry 1992, 535–37. Dordrecht: Springer Netherlands, 1993. http://dx.doi.org/10.1007/978-94-011-1474-5_156.

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Etzkorn, Felicia A., Jeremy M. Travins, and Scott A. Hart. "Rare protein turns: γ-turn, helix-turn-helix, and cis-proline mimics." In Advances in Amino Acid Mimetics and Peptidomimetics Volume 2, 125–63. Elsevier, 1999. http://dx.doi.org/10.1016/s1874-5113(99)80006-9.

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"12.2 Synthesis of Peptides Incorporating γ-Turn Inducers and Mimetics." In Houben-Weyl Methods of Organic Chemistry Vol. E 22c, 4th Edition Supplement, edited by Murray Goodman, Arthur Felix, Luis Moroder, and Claudio Toniolo. Stuttgart: Georg Thieme Verlag, 2004. http://dx.doi.org/10.1055/b-0035-113276.

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Journal articles
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