IDENTIFICATION OF A NOVEL AMINO-ACID, ORTHO-BROMO-L-PHENYLALANINE, IN EGG-ASSOCIATED PEPTIDES THAT ACTIVATE SPERMATOZOA

被引:7
作者
YOSHINO, K
TAKAO, T
SUHARA, M
KITAI, T
HORI, H
NOMURA, K
YAMAGUCHI, M
SHIMONISHI, Y
SUZUKI, N
机构
[1] KANAZAWA UNIV,NOTO MARINE LAB,UCHIURA,ISHIKAWA 92705,JAPAN
[2] OSAKA UNIV,INST PROT RES,SUITA,OSAKA 565,JAPAN
[3] KANAZAWA UNIV,FAC SCI,DEPT CHEM,KANAZAWA,ISHIKAWA 920,JAPAN
[4] TOKYO METROPOLITAN GERIATR HOSP & INST GERONTOL,DEPT BIOCHEM,ITABASHI KU,TOKYO 173,JAPAN
关键词
D O I
10.1021/bi00239a018
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Eight sperm-activating peptides containing a novel amino acid were isolated from the egg jelly of the sea urchin Tripneustes gratilla. Accurate mass measurement of the peptide in FAB mass spectrometry showed that the mass of the novel amino acid residue was 224.978. On the basis of the isotopic ion distribution and the degree of unsaturation, the mass value indicated that the elemental composition of the amino acid residue was C9H8O1N Br1, suggesting that the novel amino acid was bromophenylalanine. Proton NMR spectroscopy, amino acid analysis, and RP-HPLC with three synthetic isomers of bromophenylalanine demonstrated that o-bromophenylalanine was the novel amino acid. Derivatization of the amino acid with Marfey's reagent, (1-fluoro-2,4-dinitrophen-5-yl)-L-alanine amide (FDAA), further indicated that the amino acid was the L-isomer. In other sperm-activating peptides isolated from the egg jelly of the sea urchin, both m- and p-bromophenylalanines were discovered. The presence of m-bromophenylalanine has not been previously reported in natural products, while p-bromophenylalanine is found in theonellamide F, an antifungal bicyclic peptide from a marine sponge.
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页码:6203 / 6209
页数:7
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