Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093-0358, USA.
J Nat Prod. 2013 Mar 22;76(3):374-81. doi: 10.1021/np300744y. Epub 2012 Dec 26.
Halisphingosines A (1) and B (2), modified long-chain sphingoid bases, from the marine sponge Haliclona tubifera collected in Brazil, were characterized after conversion to their N-Boc derivatives. The 2R,3R,6R configuration of halisphingosine A, a compound first reported from Haliclona sp. from South Korea, was confirmed using a novel CD approach: deconvolution of exciton coupling from mono- and trinaphthoyl derivatives obtained by derivatization of the natural product. The sensitive CD deconvolution method, applicable to submilligram samples, simultaneously predicted the relative and absolute configuration of three stereocenters in halisphingosine A with precision and accuracy. Halisphingosine B was assigned by correlation to halisphingosine A.
从巴西采集的海洋海绵 Haliclona tubifera 中分离得到的改性长链神经酰胺碱基 Halisphingosines A(1)和 B(2),在转化为其 N-Boc 衍生物后进行了表征。Halisphingosine A 的 2R,3R,6R 构型得到了确认,该化合物最初是从韩国的 Haliclona sp.中报道的,使用一种新颖的 CD 方法进行了去卷积:通过对天然产物进行衍生化获得的单和三萘酰基衍生物的外消旋耦合的去卷积。适用于亚毫克样品的灵敏 CD 去卷积方法,精确且准确地同时预测了 halisphingosine A 中三个立体中心的相对和绝对构型。Halisphingosine B 通过与 halisphingosine A 的相关性进行了分配。