ISOLATION ON TREHALAMINE, THE AGLYCON OF TREHAZOLIN, FROM MICROBIAL BROTHS AND CHARACTERIZATION OF TREHAZOLIN RELATED COMPOUNDS
Trehalamine, (3aR, 4R, 5S, 6S, 6aS)-2-amino-4-(hydroxymethyl)-3a, 5, 6, 6a-tetrahydro-4H-cyclopent[d]oxazole-4, 5, 6-triol (1) and D-glucose were obtained by acid hydrolysis of trehazolin (3), a trehalase inhibitor produced by actinomycetes. More vigorous hydrolytic treatment of trehazolin afforded...
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| Published in | Journal of antibiotics Vol. 46; no. 7; pp. 1116 - 1125 |
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| Main Authors | , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
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Tokyo
JAPAN ANTIBIOTICS RESEARCH ASSOCIATION
1993
Japan Antibiotics Research Association |
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| Abstract | Trehalamine, (3aR, 4R, 5S, 6S, 6aS)-2-amino-4-(hydroxymethyl)-3a, 5, 6, 6a-tetrahydro-4H-cyclopent[d]oxazole-4, 5, 6-triol (1) and D-glucose were obtained by acid hydrolysis of trehazolin (3), a trehalase inhibitor produced by actinomycetes. More vigorous hydrolytic treatment of trehazolin afforded an aminocyclitol, (1R, 2S, 3R, 4S, 5R)-5-ammo-l-(hydroxymethyl)cyclopentane-1, 2, 3, 4-tetraol (2). Trehalamine, the aglycon of trehazolin, was also found in the culture broths of two trehazolin producing strains, Micromonospora sp. SANK 62390 and Amycolatopsis sp. SANK 60791. These trehazolin related compounds trehalamine (1) and 2 were poor inhibitors of trehalase (1; IC50 1.8 × 10-4 M, 2; > 5.0 × 10-4 M). On the other hand they inhibited more potently rat intestinal sucrase (1; IC50 6.8 × 10-5M) and sweet almond β-glucosidase (2; IC50 5.6× 10-6M) than trehazolin. |
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| AbstractList | Trehalamine, (3aR,4R,5S,6S,6aS)-2-amino-4-(hydroxymethyl)-3a,5,6,6a- tetrahydro-4H-cyclo-pent[d]oxazole-4,5,6-triol (1) and D-glucose were obtained by acid hydrolysis of trehazolin (3), a trehalase inhibitor produced by actinomycetes. More vigorous hydrolytic treatment of trehazolin afforded an aminocyclitol, (1R,2S,3R,4S,5R)-5-amino-1- (hydroxymethyl)cyclopentane-1,2,3,4-tetraol (2). Trehalamine, the aglycon of trehazolin, was also found in the culture broths of two trehazolin producing strains, Micromonospora sp. SANK 62390 and Amycolatopsis sp. SANK 60791. These trehazolin related compounds trehalamine (1) and 2 were poor inhibitors of trehalase (1; IC50 1.8 x 10(-4) M, 2; > 5.0 x 10(-4) M). On the other hand they inhibited more potently rat intestinal sucrase (1; IC50 6.8 x 10(-5) M) and sweet almond beta-glucosidase (2; IC50 5.6 x 10(-6) M) than trehazolin. Trehalamine, (3aR,4R,5S,6S,6aS)-2-amino-4-(hydroxymethyl)-3a,5,6,6a- tetrahydro-4H-cyclo-pent[d]oxazole-4,5,6-triol (1) and D-glucose were obtained by acid hydrolysis of trehazolin (3), a trehalase inhibitor produced by actinomycetes. More vigorous hydrolytic treatment of trehazolin afforded an aminocyclitol, (1R,2S,3R,4S,5R)-5-amino-1- (hydroxymethyl)cyclopentane-1,2,3,4-tetraol (2). Trehalamine, the aglycon of trehazolin, was also found in the culture broths of two trehazolin producing strains, Micromonospora sp. SANK 62390 and Amycolatopsis sp. SANK 60791. These trehazolin related compounds trehalamine (1) and 2 were poor inhibitors of trehalase (1; IC50 1.8 x 10(-4) M, 2; > 5.0 x 10(-4) M). On the other hand they inhibited more potently rat intestinal sucrase (1; IC50 6.8 x 10(-5) M) and sweet almond beta-glucosidase (2; IC50 5.6 x 10(-6) M) than trehazolin. Trehalamine, (3aR, 4R, 5S, 6S, 6aS)-2-amino-4-(hydroxymethyl)-3a, 5, 6, 6a-tetrahydro-4H-cyclopent[d]oxazole-4, 5, 6-triol (1) and D-glucose were obtained by acid hydrolysis of trehazolin (3), a trehalase inhibitor produced by actinomycetes. More vigorous hydrolytic treatment of trehazolin afforded an aminocyclitol, (1R, 2S, 3R, 4S, 5R)-5-ammo-l-(hydroxymethyl)cyclopentane-1, 2, 3, 4-tetraol (2). Trehalamine, the aglycon of trehazolin, was also found in the culture broths of two trehazolin producing strains, Micromonospora sp. SANK 62390 and Amycolatopsis sp. SANK 60791. These trehazolin related compounds trehalamine (1) and 2 were poor inhibitors of trehalase (1; IC50 1.8 × 10-4 M, 2; > 5.0 × 10-4 M). On the other hand they inhibited more potently rat intestinal sucrase (1; IC50 6.8 × 10-5M) and sweet almond β-glucosidase (2; IC50 5.6× 10-6M) than trehazolin. |
| Author | ANDO, OSAMU SATO, AKIRA NAKAJIMA, MUTSUO HAMANO, KIYOSHI OKAZAKI, TAKAO KINOSHITA, TAKESHI ITOI, KAZUKO ENOKITA, RYUZO HARUYAMA, HIDEYUKI TAKAHASHI, SHUJI TAKAMATSU, YASUYUKI |
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| Keywords | β-D-Glucosidase Molecular structure Enzyme Micromonosporaceae Micromonospora Aglycone Amycolatopsis Enzyme inhibitor Pseudonocardiaceae Actinomycetales Sucrose α-D-glucohydrolase Microbial origin Bacteria Isolation Actinomycetes Physicochemical properties |
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| Snippet | Trehalamine, (3aR, 4R, 5S, 6S, 6aS)-2-amino-4-(hydroxymethyl)-3a, 5, 6, 6a-tetrahydro-4H-cyclopent[d]oxazole-4, 5, 6-triol (1) and D-glucose were obtained by... Trehalamine, (3aR,4R,5S,6S,6aS)-2-amino-4-(hydroxymethyl)-3a,5,6,6a- tetrahydro-4H-cyclo-pent[d]oxazole-4,5,6-triol (1) and D-glucose were obtained by acid... |
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| SubjectTerms | Actinobacteria - classification Actinobacteria - metabolism Animals Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents Applied microbiology Biological and medical sciences Bombyx Chemotherapic agents Disaccharides - metabolism Fundamental and applied biological sciences. Psychology Glycoside Hydrolases - antagonists & inhibitors Hydrolysis Microbiology Micromonospora - classification Micromonospora - metabolism Molecular Structure Nuts Oxazoles - chemistry Oxazoles - isolation & purification Oxazoles - pharmacology Rats |
| Title | ISOLATION ON TREHALAMINE, THE AGLYCON OF TREHAZOLIN, FROM MICROBIAL BROTHS AND CHARACTERIZATION OF TREHAZOLIN RELATED COMPOUNDS |
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