Thoen Jason C, Morales-Ramos Angel I, Lipton Mark A
Department of Chemistry, Purdue University, West Lafayette, Indiana 47907-1393, USA.
Org Lett. 2002 Dec 12;4(25):4455-8. doi: 10.1021/ol0269852.
[reaction: see text] The novel amino acid residue (2R,3R,4S)-4-amido-7-guanidino-2,3-dihydroxyheptanoic acid (AGDHE, 3), a constituent of the cyclic depsipeptides callipeltins A and D, and its (2S,3S,4S) diastereomer were synthesized from a protected L-ornithine derivative in 13 steps (15% overall yield), and its configurational assignment was reexamined by (1)H NMR.
[反应:见正文] 新型氨基酸残基(2R,3R,4S)-4-酰胺基-7-胍基-2,3-二羟基庚酸(AGDHE,3)是环缩肽callipeltins A和D的组成部分,其(2S,3S,4S)非对映异构体由一种受保护的L-鸟氨酸衍生物经13步合成(总产率15%),并通过1H NMR重新确定其构型。