کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5272905 1385476 2010 5 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
On-resin cyclization and antimicrobial activity of Laterocidin and its analogues
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
On-resin cyclization and antimicrobial activity of Laterocidin and its analogues
چکیده انگلیسی

Total synthesis of cyclodecapeptide antibiotics from Bacillus laterosporus, laterocidin and its analogues, was accomplished for the first time by solid-phase peptide synthesis followed by traceless on-resin cyclization of the linear precursors with protection of α-carboxyl group on the Asp residue by Dmab as a temporary blocking group for on-resin head-to-tail cyclization, in which the carboxyl group of side chain of Asp was linked to Rink resin. Single alanine substitution or Asn substitution (Asp10→Asn10) demonstrated improvements in antibacterial activity. Of note, d-Phe2 and Pro4 play an important role in on-resin head-to-tail cyclization and exerting antibacterial activity of Laterocidin.

Total synthesis of naturally occurring Laterocidin and its alanine-scanning analogues with the side chain carboxyl group of Aspartate linked to Rink resin, and the α-carboxyl group of Aspartate protected by Dmab group as a temporary blocking group for on-resin head-to-tail cyclization of the linear precursor is reported.

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron Letters - Volume 51, Issue 9, 3 March 2010, Pages 1257-1261
نویسندگان
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