Academic Journal
Synthesis and Conformational Analysis of Methyl N‐Alanyl‐1′‐aminoferrocene‐1‐carboxylate
| العنوان: | Synthesis and Conformational Analysis of Methyl N‐Alanyl‐1′‐aminoferrocene‐1‐carboxylate |
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| المؤلفون: | Barišić, Lidija, Kovačević, Monika, Mamić, Marija, Kodrin, Ivan, Mihalić, Zlatko, Rapić, Vladimir |
| المصدر: | European Journal of Inorganic Chemistry ; volume 2012, issue 11, page 1810-1822 ; ISSN 1434-1948 1099-0682 |
| بيانات النشر: | Wiley |
| سنة النشر: | 2012 |
| المجموعة: | Wiley Online Library (Open Access Articles via Crossref) |
| الوصف: | Structurally different ferrocene peptides I – VI exhibit considerable conformational differences. This study has explored the structural properties of VII [Y‐AA‐Fca‐OMe; Y = di‐ tert ‐butyl dicarbonate (Boc), acetyl (Ac); AA = L ‐Ala, D ‐Ala; Fca = 1′‐aminoferrocene‐1‐carboxylic acid] with an exchanged sequence of constituent amino acids relative to VI (Y‐Fca‐AA‐OMe; Y = Boc, Ac; AA = L ‐Ala, D ‐Ala). The ferrocene peptides VII were obtained by coupling C ‐protected Fca with Boc‐ L ‐Ala‐OH and Boc‐ D ‐Ala‐OH, respectively. The Boc protecting groups of the obtained conjugates Boc‐AA‐Fca‐OMe ( 2a , AA = L ‐Ala; 2b , AA = D ‐Ala) were converted to sterically less demanding Ac groups to give Ac‐AA‐Fca‐OMe ( 3a , AA = L ‐Ala; 3b , AA = D ‐Ala). In order to examine their conformational properties, peptides VII were subjected to spectroscopic analysis (IR, 1 H NMR, CD) and molecular modeling (DFT). The alteration of peptides VI into VII significantly influenced their conformational properties. Conjugates VI were stabilized through interchain hydrogen bonding, whereas inter‐ and intrachain hydrogen bonds were established in their constitutional isomers VII . The replacement of the bulky Boc group with an Ac group did not cause major conformational changes, and the absolute configuration of the alanine chiral centers did not affect the conformational properties. |
| نوع الوثيقة: | article in journal/newspaper |
| اللغة: | English |
| DOI: | 10.1002/ejic.201101270 |
| الاتاحة: | http://dx.doi.org/10.1002/ejic.201101270 https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1002%2Fejic.201101270 https://onlinelibrary.wiley.com/doi/pdf/10.1002/ejic.201101270 https://onlinelibrary.wiley.com/doi/full-xml/10.1002/ejic.201101270 |
| Rights: | http://onlinelibrary.wiley.com/termsAndConditions#vor |
| رقم الانضمام: | edsbas.1614251A |
| قاعدة البيانات: | BASE |
| DOI: | 10.1002/ejic.201101270 |
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