Tylopeptin A
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| Category | Antibiotics |
| Catalog number | BBF-02729 |
| CAS | |
| Molecular Weight | 1553.84 |
| Molecular Formula | C73H120N18O19 |
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Description
Tylopeptin A is originally isolated from Tylopilus neofelleus and it has anti-gram-positive bacteria activity.
Specification
| IUPAC Name | (2S)-2-[[(2S)-2-[[(2R)-2-[[2-[[(2S)-2-[[(2S)-2-acetamido-3-(1H-indol-3-yl)propanoyl]amino]-3-methylbutanoyl]amino]-2-methylpropanoyl]amino]-2-methylbutanoyl]amino]propanoyl]amino]-N-[(2S)-1-[[1-[[(2S)-1-[[1-[[(2S)-1-[[(2S)-1-[[1-[[(2S)-5-amino-1-[[(2S)-1-hydroxy-4-methylpentan-2-yl]amino]-1,5-dioxopentan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-1-oxopropan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-methyl-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]pentanediamide |
| Canonical SMILES | CCC(C)(C(=O)NC(C)C(=O)NC(CCC(=O)N)C(=O)NC(C)C(=O)NC(C)(C)C(=O)NC(CO)C(=O)NC(C)(C)C(=O)NC(C)C(=O)NC(CC(C)C)C(=O)NC(C)(C)C(=O)NC(CCC(=O)N)C(=O)NC(CC(C)C)CO)NC(=O)C(C)(C)NC(=O)C(C(C)C)NC(=O)C(CC1=CNC2=CC=CC=C21)NC(=O)C |
| InChI | InChI=1S/C73H120N18O19/c1-21-73(20,91-67(109)72(18,19)90-63(105)54(38(6)7)86-60(102)50(80-42(11)94)32-43-33-76-46-25-23-22-24-45(43)46)68(110)79-40(9)55(97)82-47(26-28-52(74)95)58(100)77-41(10)57(99)87-70(14,15)66(108)85-51(35-93)62(104)89-69(12,13)64(106)78-39(8)56(98)83-49(31-37(4)5)61(103)88-71(16,17)65(107)84-48(27-29-53(75)96)59(101)81-44(34-92)30-36(2)3/h22-25,33,36-41,44,47-51,54,76,92-93H,21,26-32,34-35H2,1-20H3,(H2,74,95)(H2,75,96)(H,77,100)(H,78,106)(H,79,110)(H,80,94)(H,81,101)(H,82,97)(H,83,98)(H,84,107)(H,85,108)(H,86,102)(H,87,99)(H,88,103)(H,89,104)(H,90,105)(H,91,109)/t39-,40-,41-,44-,47-,48-,49-,50-,51-,54-,73+/m0/s1 |
| InChI Key | ZXSAQOASWXTEMJ-SYWGTLAGSA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Melting Point | 215-218°C |
Reference Reading
1. Tylopeptins A and B, new antibiotic peptides from Tylopilus neofelleus
S J Lee, B S Yun, D H Cho, I D Yoo J Antibiot (Tokyo). 1999 Nov;52(11):998-1006. doi: 10.7164/antibiotics.52.998.
Two new peptides, tylopeptins A and B, were isolated from the methanol extract of the fruiting body of the mushroom, Tylopilus neofelleus. These peptides were identified as peptaibols possessing an acetylated N-terminal residue, fourteen amino acids, and leucinol as the C-terminal amino alcohol. Sequential determination and complete 1H and 13C resonance assignments were based on positive ion FAB mass spectroscopy and two dimensional NMR techniques. These peptides were subsequently shown to be active against some gram-positive bacteria, but inactive against pathogenic fungi and gram-negative bacteria.
2. Chilenopeptins A and B, Peptaibols from the Chilean Sepedonium aff. chalcipori KSH 883
Alexander Otto, Annegret Laub, Lucile Wendt, Andrea Porzel, Jürgen Schmidt, Götz Palfner, José Becerra, Dirk Krüger, Marc Stadler, Ludger Wessjohann, Bernhard Westermann, Norbert Arnold J Nat Prod. 2016 Apr 22;79(4):929-38. doi: 10.1021/acs.jnatprod.5b01018. Epub 2016 Mar 8.
The Chilean Sepedonium aff. chalcipori strain KSH 883, isolated from the endemic Boletus loyo Philippi, was studied in a polythetic approach based on chemical, molecular, and biological data. A taxonomic study of the strain using molecular data of the ITS, EF1-α, and RPB2 barcoding genes confirmed the position of the isolated strain within the S. chalcipori clade, but also suggested the separation of this clade into three different species. Two new linear 15-residue peptaibols, named chilenopeptins A (1) and B (2), together with the known peptaibols tylopeptins A (3) and B (4) were isolated from the semisolid culture of strain KSH 883. The structures of 1 and 2 were elucidated on the basis of HRESIMS(n) experiments in conjunction with comprehensive 1D and 2D NMR analysis. Thus, the sequence of chilenopeptin A (1) was identified as Ac-Aib(1)-Ser(2)-Trp(3)-Aib(4)-Pro(5)-Leu(6)-Aib(7)-Aib(8)-Gln(9)-Aib(10)-Aib(11)-Gln(12)-Aib(13)-Leu(14)-Pheol(15), while chilenopeptin B (2) differs from 1 by the replacement of Trp(3) by Phe(3). Additionally, the total synthesis of 1 and 2 was accomplished by a solid-phase approach, confirming the absolute configuration of all chiral amino acids as l. Both the chilenopeptins (1 and 2) and tylopeptins (3 and 4) were evaluated for their potential to inhibit the growth of phytopathogenic organisms.
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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 ╳
