Isolation and absolute configuration of SMTP-0, a simplest congener of the SMTP family nonlysine-analog plasminogen modulators

被引:24
作者
Hasumi, Keiji [1 ]
Hasegawa, Keiko [1 ]
Kitano, Yoshikazu [1 ]
机构
[1] Tokyo Noko Univ, Dept Appl Biol Sci, Fuchu, Tokyo 1838509, Japan
关键词
nonlysine-analog plasminogen modulator; absolute configuration; Stachybotrys microspora; microbial triprenyl phenols; modified Mosher method;
D O I
10.1038/ja.2007.60
中图分类号
Q81 [生物工程学(生物技术)]; Q93 [微生物学];
学科分类号
071005 ; 0836 ; 090102 ; 100705 ;
摘要
SMTP-0, a new simple congener of the SMTP nonlysine-analog plasminogen modulators, was isolated from a culture of Stachybotrys microspora. Based on the physico-chemical data, SMTP-O was shown to be an enantiomer of the antimicrobial compound stachybotrin B. The absolute configuration of SMTP-0 was determined by the modified Mosher method. The stereochemistry was further confirmed using an epimer of SMTP-O. Unlike most SMTPs with an amino acid side chain linked to the nitrogen atom of the lactam moiety, SMTP-0, which lacks the N-linked side chain, showed no plasminogen modulator activity.
引用
收藏
页码:463 / 468
页数:6
相关论文
共 21 条
[1]   Lysine-50 is a likely site for anchoring the plasminogen N-terminal peptide to lysine-binding kringles [J].
An, SSA ;
Carreño, C ;
Marti, DN ;
Schaller, J ;
Albericio, F ;
Llinas, M .
PROTEIN SCIENCE, 1998, 7 (09) :1960-1969
[2]  
AOYAMA T, 1984, CHEM PHARM BULL, V32, P3759
[3]   Molecular genetics of the fibrinolytic and coagulation systems in haemostasis, thrombogenesis, restenosis and atherosclerosis [J].
Carmeliet, P ;
Collen, D .
CURRENT OPINION IN LIPIDOLOGY, 1997, 8 (02) :118-125
[4]   Children and citizenship in Britain - A case for a socially interdependent model of citizenship [J].
Cockburn, T .
CHILDHOOD-A GLOBAL JOURNAL OF CHILD RESEARCH, 1998, 5 (01) :99-117
[5]   ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].
DALE, JA ;
DULL, DL ;
MOSHER, HS .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&
[6]   A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES [J].
DESS, DB ;
MARTIN, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) :7277-7287
[7]   MOLECULAR-CLONING AND CHARACTERIZATION OF A FULL-LENGTH CDNA CLONE FOR HUMAN-PLASMINOGEN [J].
FORSGREN, M ;
RADEN, B ;
ISRAELSSON, M ;
LARSSON, K ;
HEDEN, LO .
FEBS LETTERS, 1987, 213 (02) :254-260
[8]   ENDOTHELIAL CELL-MEDIATED CONVERSION OF GLU-PLASMINOGEN TO LYS-PLASMINOGEN - FURTHER EVIDENCE FOR ASSEMBLY OF THE FIBRINOLYTIC SYSTEM ON THE ENDOTHELIAL-CELL SURFACE [J].
HAJJAR, KA ;
NACHMAN, RL .
JOURNAL OF CLINICAL INVESTIGATION, 1988, 82 (05) :1769-1778
[9]   Isolation of SMTP-3, 4, 5 and -6, novel analogs of staplabin, and their effects on plasminogen activation and fibrinolysis [J].
Hasumi, K ;
Ohyama, S ;
Kohyama, T ;
Ohsaki, Y ;
Takayasu, R ;
Endo, A .
JOURNAL OF ANTIBIOTICS, 1998, 51 (12) :1059-1068
[10]   SMTP-4D,-5D,-6D,-7D and-8D, a new series of the non-lysine-analog plasminogen modulators with a D-amino acid moiety [J].
Hu, WM ;
Kitano, Y ;
Hasumi, K .
JOURNAL OF ANTIBIOTICS, 2003, 56 (10) :832-837