InChI=1S/C13H20N6O3S/c14-2-1-3-23-4-7-9(20)10(21)13(22-7)19-6-18-8-11(15)16-5-17-12(8)19/h5-7,9-10,13,20-21H,1-4,14H2,(H2,15,16,17)/t7-,9-,10-,13-/m1/s1 |
FUSRAALGPJJIRO-QYVSTXNMSA-N |
NCCCSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n1cnc2c(N)ncnc12 |
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Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
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View more via ChEBI Ontology
5'-S-(3-aminopropyl)-5'-thioadenosine
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53186-57-5
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CAS Registry Number
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ChemIDplus
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577457
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Reaxys Registry Number
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Reaxys
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Ito S (1983) Isolation of S-adenosyl-3-thiopropylamine. Methods in enzymology 94, 463-464 [PubMed:6621400] | Hibasami H, Borchardt RT, Chen SY, Coward JK, Pegg AE (1980) Studies of inhibition of rat spermidine synthase and spermine synthase. The Biochemical journal 187, 419-428 [PubMed:7396856] [show Abstract] 1. S-Adenosyl-l-methionine, S-adenosyl-l-homocysteine, 5'-methylthioadenosine and a number of analogues having changes in the base, sugar or amino acid portions of the molecule were tested as potential inhibitors of spermidine synthase and spermine synthase from rat ventral prostate. 2. S-Adenosyl-l-methionine was inhibitory to these reactions, as were other nucleosides containing a sulphonium centre. The most active of these were S-adenosyl-l-ethionine, S-adenosyl-4-methylthiobutyric acid, S-adenosyl-d-methionine and S-tubercidinylmethionine, which were all comparable in activity with S-adenosylmethionine itself, producing 70-98% inhibition at 1mm concentrations. Spermine synthase was somewhat more sensitive than spermidine synthase. 3. 5'-Methylthioadenosine, 5'-ethylthioadenosine and 5'-methylthiotubercidin were all powerful inhibitors of both enzymes, giving 50% inhibition of spermine synthase at 10-15mum and 50% inhibition of spermidine synthase at 30-45mum. 4. S-Adenosyl-l-homocysteine was a weak inhibitor of spermine synthase and practically inactive against spermidine synthase. Analogues of S-adenosylhomocysteine lacking either the carboxy or the amino group of the amino acid portion were somewhat more active, as were derivatives in which the ribose ring had been opened by oxidation. The sulphoxide and sulphone derivatives of decarboxylated S-adenosyl-l-homocysteine and the sulphone of S-adenosyl-l-homocysteine were quite potent inhibitors and were particularly active against spermidine synthase (giving 50% inhibition at 380, 50 and 20mum respectively). 5. These results are discussed in terms of the possible regulation of polyamine synthesis by endogenous nucleosides and the possible value of some of the inhibitory substances in experimental manipulations of polyamine concentrations. It is suggested that 5'-methylthiotubercidin and the sulphone of S-adenosylhomocysteine or of S-adenosyl-3-thiopropylamine may be particularly valuable in this respect. | Ito S, Nicol JA (1976) Isolation of S-adenosyl-3-thiopropylamine from the eye of the sea catfish (Arius felis). The Biochemical journal 153, 567-570 [PubMed:942371] [show Abstract] A method is reported for the separation of S-adenosyl-3-methylthiopropylamine and other basic compounds in the eye of the sea catfish (Arius felis) by ion-exchange chromatography on CM-Sephadex. One of the basic compounds was isolated in crystalline form and was shown to be S-adenosyl-3-thiopropylamine by chemical and spectroscopic characterizations and by comparison with a synthetic sample. |
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