Tolypomycin Y
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| Category | Antibiotics |
| Catalog number | BBF-02698 |
| CAS | 23412-26-2 |
| Molecular Weight | 822.89 |
| Molecular Formula | C43H54N2O14 |
| Purity | 96% |
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Description
Tolypomycin Y is produced by the strain of Str. tolypophorus B2847. It has a broad-spectrum antimicrobial effect, which protects mice infected with gram-positive bacteria, and also has an inhibitory effect on vaccine virus.
Specification
| Synonyms | NSC-177383; Tolypromycin Y |
| IUPAC Name | [(9E,22Z)-2,15,17-trihydroxy-28-(6-hydroxy-2-methyloxan-3-yl)imino-11-methoxy-3,7,12,14,16,23-hexamethyl-6,21,24,30-tetraoxo-8,31-dioxa-25-azapentacyclo[24.3.1.14,7.05,29.018,20]hentriaconta-1(29),2,4,9,22,26-hexaen-13-yl] acetate |
| Canonical SMILES | CC1C(C=COC2(C(=O)C3=C(O2)C(=C(C4=C3C(=NC5CCC(OC5C)O)C=C(C4=O)NC(=O)C(=CC(=O)C6CC6C(C(C(C(C1OC(=O)C)C)O)C)O)C)O)C)C)OC |
| InChI | InChI=1S/C43H54N2O14/c1-17-14-29(47)24-15-25(24)36(50)19(3)35(49)20(4)39(58-23(7)46)18(2)30(55-9)12-13-56-43(8)41(53)34-32-27(44-26-10-11-31(48)57-22(26)6)16-28(45-42(17)54)38(52)33(32)37(51)21(5)40(34)59-43/h12-14,16,18-20,22,24-26,30-31,35-36,39,48-51H,10-11,15H2,1-9H3,(H,45,54)/b13-12+,17-14-,44-27? |
| InChI Key | RYCBEGMWBUYSAD-NLAQSMJJSA-N |
Properties
| Appearance | Yellow Acicular Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; viruses |
| Boiling Point | 995.5°C at 760 mmHg |
| Melting Point | <300°C |
| Density | 1.2107 g/cm3 |
Reference Reading
1. Synthesis and antibacterial activity of some derivatives of tolypomycinone. Relationship between structure and activity in ansamycins
P Bellomo, M Brufani, E Marchi, G Mascellani, W Melloni, L Montecchi, L Stanzani J Med Chem. 1977 Oct;20(10):1287-91. doi: 10.1021/jm00220a012.
3-Aminotolypomycinoes and 3,16-diamino-16,17-dihydrotolypomycinones are formed by the addition of primary and secondary amines to tolypomycinone, obtained by mild hydrolysis of the antibiotic tolypomycin Y.3-Amino-16,17-dihydrotolypomycinones are formed by the addition of primary and secondary amines to 16,17-dihydrotolypomycinone. In vitro microbiological tests showed high antibacterial activity in compounds obtained by the addition of primary amines, which must be unbranched in the alpha position to the nitrogen atom to position 3 of the naphthoquinone ring. The relationship between structure and activity is described, and evidence is presented that hydrogen bonding between the amino NH bonded to C3 and the amide CO of tolypomycinone is very important for biological activity.
2. MIC values do not predict the intraphagocytic killing of Staphylococcus aureus by naphthalenic ansamycins
V P Marshall, J I Cialdella, G M Ohlmann, G D Gray J Antibiot (Tokyo). 1983 Nov;36(11):1549-60. doi: 10.7164/antibiotics.36.1549.
Ten naphthalenic ansamycins were compared for their ability to kill extracellular or phagocytosed Staphylococcus aureus 502A. These included rifamycins, streptovaricins and tolypomycin Y. Although the compounds differed markedly in killing extracellular S. aureus, there was surprisingly little difference between them in assisting human leukocytes to kill phagocytosed S. aureus. In fact, when compared to rifampin, some ansamycins that were less effective in killing extracellular bacteria were more effective in killing phagocytosed bacteria. These data, together with an analysis of structure and activity, suggested that a specific transport mechanism might be involved. First considered was a vitamin K transport mechanism. Indeed warfarin, a vitamin K antagonist, blocked the ability of rifampin to kill phagocytosed S. aureus, as did the coumarins, novobiocin and coumarin-3-carboxylic acid. However, direct evidence for a vitamin K transport mechanism could not be obtained using vitamin K preparations. The fused phenolic, bicyclic system common to all of these ansamycins was tentatively considered to be the portion necessary for phagocyte penetration.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
