Tsuda M, Muraoka Y, Takeuchi T, Sekizawa R, Umezawa K
Institute of Microbial Chemistry, Tokyo, Japan.
J Antibiot (Tokyo). 1996 Oct;49(10):1031-5. doi: 10.7164/antibiotics.49.1031.
(2S,3R)-3-Amino-2-hydroxyoctanoic acid was synthesized by Curtius rearrangement of an azide derivative of (S)-malic acid. Total syntheses of valinoctin A and its analogues were achieved by a coupling of (2S, 3R)-3-amino-2-hydroxyoctanoic acid moiety with L-valine or several other amino acids moieties. 2S configuration of 3-amino-2-hydroxyoctanoic acid moiety was found to be important for the inhibitory activity and the L-valine moiety of valinoctin A was exchangeable with other L-amino acids.
通过（S）-苹果酸的叠氮衍生物的库尔提斯重排反应合成了（2S，3R）-3-氨基-2-羟基辛酸。通过将（2S，3R）-3-氨基-2-羟基辛酸部分与L-缬氨酸或其他几种氨基酸部分偶联，实现了瓦利诺辛A及其类似物的全合成。发现3-氨基-2-羟基辛酸部分的2S构型对抑制活性很重要，并且瓦利诺辛A的L-缬氨酸部分可与其他L-氨基酸交换。
