Structure elucidation at the nanomole scale. 1. Trisoxazole macrolides and thiazole-containing cyclic peptides from the nudibranch Hexabranchus sanguineus.
Structure elucidation at the nanomole scale. 1. Trisoxazole macrolides and thiazole-containing cyclic peptides from the nudibranch Hexabranchus sanguineus.
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DOI：
10.1021/np8007649
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发表时间：
2009-04
影响因子：
5.1
通讯作者：
Molinski, Tadeusz F.
中科院分区：
文献类型：
--
作者：
Dalisay, Doralyn S.;Rogers, Evan W.;Edison, Arthur S.;Molinski, Tadeusz F.
一个Sexabranchus sanguineus的样本产生了新的卡比拉胺类似物-9-去甲基卡比拉胺B和33-甲基四氢卤代胡椒胺-以及两个新的亚微摩尔量的意外的含噻唑的环肽。Sexabranchus sanguineus是印度-太平洋地区的一个裸枝动物，已知它能隔离卡比拉米B、C和其他三恶唑大环内酯。这些环肽的结构由最先进的1 mm 1H核磁共振高温超导微低温探头记录的一维和二维核磁共振谱结合质谱图确定。除了两个脯氨酸残基外，每个肽还含有一个噻唑或恶唑修饰的氨基酸残基，以及传统的氨基酸残基。通过对多肽的酸解产物进行马菲分析，确定所有氨基酸残基均为L。这是首次报道从血吸虫中分离得到的环状噻唑肽。由于噻唑-恶唑修饰的多肽通常与蓝藻和被囊藻有关，这一发现可能暗示了以前被忽视的血吸虫的一种饮食成分。
A single specimen of Hexabranchus sanguineus, a nudibranch from the Indo-Pacific that is known to sequester kabiramides B, C and other trisoxazole macrolides, yielded new kabiramide analogs – 9-desmethylkabiramide B and 33-methyltetrahydrohalichondramide – and two new unexpected thiazole-containing cyclic peptides in sub-micromole amounts. The structures of these cyclic peptides were determined by analyses of 1D and 2D NMR spectra recorded with a state-of-the-art 1-mm 1H NMR high-temperature superconducting micro-cryoprobe, together with mass spectra. In addition to two proline residues, each peptide contains a thiazole- or oxazole-modified amino acid residue, together with conventional amino acid residues. All of the amino acid residues were L- as determined by Marfey’s analysis of the acid hydrolysates of the peptides. This is the first report of cyclic thiazole peptides from H. sanguineus. Since thiazole-oxazole modified peptides are typically associated with cyanobacteria and tunicates, the finding may imply a dietary component of the H. sanguineus that was previously overlooked.
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影响因子：
1.8
作者：
FUSETANI, N;YASUMURO, K;HASHIMOTO, K
通讯作者：
HASHIMOTO, K
影响因子：
1.8
作者：
Chattopadhyay, SK;Pattenden, G
通讯作者：
Pattenden, G
DOI：
10.1016/0022-0981(88)90225-0
发表时间：
1988-01-01
影响因子：
2
作者：
PAWLIK, JR;KERNAN, MR;FAULKNER, DJ
通讯作者：
FAULKNER, DJ
DOI：
10.1007/bf02908688
发表时间：
1984-01-01
期刊：
CARLSBERG RESEARCH COMMUNICATIONS
影响因子：
--
作者：
MARFEY, P
通讯作者：
MARFEY, P
影响因子：
3.6
作者：
KERNAN, MR;MOLINSKI, TF;FAULKNER, DJ
通讯作者：
FAULKNER, DJ