Li Gongyong, van der Donk Wilfred A
Roger Adams Laboratory, Department of Chemistry, University of Illinois at Urbana-Champaign, 600 South Mathews Avenue, Urbana, Illinois 61801, USA.
Org Lett. 2007 Jan 4;9(1):41-4. doi: 10.1021/ol062401a.
[reaction: see text] Fluorinated amino acids are useful building blocks for the preparation of biologically active peptides and peptidomimetics with increased metabolic stability. We report here the synthesis of two fluorinated amino acids, beta-difluoroalanine and gamma-difluorothreonine, as analogues of Ser and Thr, respectively. These compounds were suitably protected for Fmoc-based solid-phase peptide synthesis. Once incorporated into peptides, they may serve as alternative substrates or inhibitors of lantibiotic synthetases that posttranslationally dehydrate Ser and Thr residues to dehydroalanine and dehydrobutyrine, respectively.
[反应：见正文] 氟化氨基酸是用于制备具有更高代谢稳定性的生物活性肽和拟肽的有用构建单元。我们在此报告两种氟化氨基酸，β-二氟丙氨酸和γ-二氟苏氨酸的合成，它们分别是丝氨酸（Ser）和苏氨酸（Thr）的类似物。这些化合物经过适当保护，可用于基于芴甲氧羰基（Fmoc）的固相肽合成。一旦掺入肽中，它们可作为羊毛硫抗生素合成酶的替代底物或抑制剂，该酶可将Ser和Thr残基分别翻译后脱水为脱氢丙氨酸和脱氢丁氨酸。
