Amino asit içeren yeni indol türevleri sentezi
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Dosyalar
Tarih
2021
Yazarlar
Dergi Başlığı
Dergi ISSN
Cilt Başlığı
Yayıncı
İnönü Üniversitesi
Erişim Hakkı
info:eu-repo/semantics/openAccess
Özet
Bir benzopirol olan indol, ilk olarak 1866'da Adolf Von Baeyer tarafından indigodan elde edilmiştir. İndol, C8H7N formülüne sahip aromatik heterosiklik bir organik bileşiktir. İndole, doğal ortamda yaygın olarak bulunmaktadır ve çeşitli bakteriler tarafından üretilebilir. Hücreler arası bir sinyal molekülü olarak indol, spor oluşumu, plazmid stabilitesi, ilaç direnci ve biyofilm oluşumu dahil olmak üzere bakteriyel fizyolojinin çeşitli yönlerini düzenler. Amino asit triptofan, bir indol türevi ve nörotransmiter serotoninin öncüsüdür. Literatürde indol-3-asetik asitin amino asit konjugatlarına ait çok sayıda bilgi bulunmasına rağmen indolün homoaromatik halkasında amino asit sübstitüye türevleri bilinmemektedir. Bu nedenle, literatürde bulunmayan homoaromatik halkada amino asit içeren yeni indol türevlerinin sentezi amaçlanmıştır. Bu Yüksek Lisans tezi kapsamında, korumalı amino asitlerin 5-aminometilindol ile tepkimesinden, on adet yeni amino asit-indol konjügatı hazırlanmıştır. Yapısal benzerlik nedeniyle, 5-aminometilindol yerine N-metil-3-aminometilindol kullanılarak altı yeni amino asit-N-metil-3-aminometil indol konjugatı da sentezlenmiştir. Sentezlenen tüm bileşiklerin yapıları 1H-NMR, 13C-NMR, MS, FT-R spektroskopisi ve element analizi teknikleri ile aydınlatılmıştır. Anahtar Kelimeler: İndol, Amino asit, İndol-amino asit konjugatları
Indole, a benzopyrol, was first obtained from indigo by Adolf Von Baeyer in 1866. Indole is an aromatic heterocyclic organic compound with the formula C8H7N. Indole is widely distributed in natural environment and can be produced by a variety of bacteria. As an intercellular signaling molecule, indole regulates various aspects of bacterial physiology, including spore formation, plasmid stability, drug resistance and biofilm formation. The amino acid tryptophan is an indole derivative and precursor to the neurotransmitter serotonin. Although there is a lot of information about amino acid conjugates of indole-3-acetic acid in the literature, amino acid substituted derivatives in the homoaromatic ring of indole are not known. Therefore, the synthesis of new indole derivatives containing amino acids in the homoaromatic ring, which are not found in the literature, is aimed. Within the scope of this Master's thesis, ten new amino acid-indole conjugates were prepared by the reaction of protected amino acids with 5-aminomethylindole. Due to the structural similarity, six new amino acid-N-methyl-3-aminomethyl indole conjugates were also synthesized using N-methyl-3-aminomethylindole instead of 5-aminomethylindole. The structures of all synthesized compounds were identified by 1H-NMR, 13C-NMR, MS, FT-R spectroscopy and elemental analysis techniques. Keywords: Indole, Amino acid, Indole-amino acid conjugates
Indole, a benzopyrol, was first obtained from indigo by Adolf Von Baeyer in 1866. Indole is an aromatic heterocyclic organic compound with the formula C8H7N. Indole is widely distributed in natural environment and can be produced by a variety of bacteria. As an intercellular signaling molecule, indole regulates various aspects of bacterial physiology, including spore formation, plasmid stability, drug resistance and biofilm formation. The amino acid tryptophan is an indole derivative and precursor to the neurotransmitter serotonin. Although there is a lot of information about amino acid conjugates of indole-3-acetic acid in the literature, amino acid substituted derivatives in the homoaromatic ring of indole are not known. Therefore, the synthesis of new indole derivatives containing amino acids in the homoaromatic ring, which are not found in the literature, is aimed. Within the scope of this Master's thesis, ten new amino acid-indole conjugates were prepared by the reaction of protected amino acids with 5-aminomethylindole. Due to the structural similarity, six new amino acid-N-methyl-3-aminomethyl indole conjugates were also synthesized using N-methyl-3-aminomethylindole instead of 5-aminomethylindole. The structures of all synthesized compounds were identified by 1H-NMR, 13C-NMR, MS, FT-R spectroscopy and elemental analysis techniques. Keywords: Indole, Amino acid, Indole-amino acid conjugates
Açıklama
Anahtar Kelimeler
Kimya, Chemistry
Kaynak
WoS Q Değeri
Scopus Q Değeri
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Künye
Yıldırım, N. (2021). Amino asit içeren yeni indol türevleri sentezi. Yayınlanmış Yüksek Lisans Tezi, İnönü Üniversitesi.
