Hypelcin A-I
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| Category | Antibiotics |
| Catalog number | BBF-01488 |
| CAS | 93397-17-2 |
| Molecular Weight | 1929.30 |
| Molecular Formula | C89H153N23O24 |
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Description
Hypelcin A-I is originally isolated from Hypocrea peltata. It has anti-gram-negative bacterial and fungal activity.
Specification
| Synonyms | Ac-Aib-Pro-Aib-Ala-Aib-Aib-Gln-Aib-Leu-Aib-Gly-Aib-Aib-Pro-Val-Aib-Aib-Gln-Gln-Leu-ol |
| IUPAC Name | (2S)-2-[[(2S)-2-[[2-[[2-[[(2S)-2-[[(2S)-1-[2-[[2-[[2-[[2-[[(2S)-2-[[2-[[(2S)-2-[[2-[[2-[[(2S)-2-[[2-[[(2S)-1-(2-acetamido-2-methylpropanoyl)pyrrolidine-2-carbonyl]amino]-2-methylpropanoyl]amino]propanoyl]amino]-2-methylpropanoyl]amino]-2-methylpropanoyl]amino]-5-amino-5-oxopentanoyl]amino]-2-methylpropanoyl]amino]-4-methylpentanoyl]amino]-2-methylpropanoyl]amino]acetyl]amino]-2-methylpropanoyl]amino]-2-methylpropanoyl]pyrrolidine-2-carbonyl]amino]-3-methylbutanoyl]amino]-2-methylpropanoyl]amino]-2-methylpropanoyl]amino]-5-amino-5-oxopentanoyl]amino]-N-[(2S)-1-hydroxy-4-methylpentan-2-yl]pentanediamide |
| Canonical SMILES | CC(C)CC(CO)NC(=O)C(CCC(=O)N)NC(=O)C(CCC(=O)N)NC(=O)C(C)(C)NC(=O)C(C)(C)NC(=O)C(C(C)C)NC(=O)C1CCCN1C(=O)C(C)(C)NC(=O)C(C)(C)NC(=O)CNC(=O)C(C)(C)NC(=O)C(CC(C)C)NC(=O)C(C)(C)NC(=O)C(CCC(=O)N)NC(=O)C(C)(C)NC(=O)C(C)(C)NC(=O)C(C)NC(=O)C(C)(C)NC(=O)C2CCCN2C(=O)C(C)(C)NC(=O)C |
| InChI | InChI=1S/C89H153N23O24/c1-45(2)41-50(44-113)95-63(120)51(33-36-57(90)115)96-64(121)52(34-37-58(91)116)97-73(130)83(15,16)109-77(134)87(23,24)107-69(126)61(47(5)6)100-67(124)55-31-29-39-111(55)79(136)89(27,28)110-75(132)85(19,20)102-60(118)43-93-70(127)80(9,10)105-66(123)54(42-46(3)4)99-72(129)82(13,14)104-65(122)53(35-38-59(92)117)98-74(131)84(17,18)108-76(133)86(21,22)103-62(119)48(7)94-71(128)81(11,12)106-68(125)56-32-30-40-112(56)78(135)88(25,26)101-49(8)114/h45-48,50-56,61,113H,29-44H2,1-28H3,(H2,90,115)(H2,91,116)(H2,92,117)(H,93,127)(H,94,128)(H,95,120)(H,96,121)(H,97,130)(H,98,131)(H,99,129)(H,100,124)(H,101,114)(H,102,118)(H,103,119)(H,104,122)(H,105,123)(H,106,125)(H,107,126)(H,108,133)(H,109,134)(H,110,132)/t48-,50-,51-,52-,53-,54-,55-,56-,61-/m0/s1 |
| InChI Key | KHUSJDWGFDJJCN-HGEPYVCOSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-negative bacteria; fungi |
| Melting Point | 265-266°C |
Reference Reading
1. Ion-channels formed by hypelcins, antibiotic peptides, in planar bilayer lipid membranes
N Koide, K Asami, T Fujita Biochim Biophys Acta. 1997 May 22;1326(1):47-53. doi: 10.1016/s0005-2736(97)00005-9.
Ion-channel properties of native hypelcins (HP) A-I, A-V and B-V isolated from Hypocrea peltata and a synthetic analog, HP-A-Pheol, were studied in planar bilayer lipid membranes by a single-channel recording technique. The native and synthetic hypelcins formed ion-channels with three conductance levels for 3 mole dm(-3) KCl: < or = 0.09 nS at 225 mV (level 0, only detectable at voltages above 200 mV), approximately 0.6 nS at 150 mV (level 1, most common level) and approximately 3 nS at 150 mV (level 2). The effects of the C-terminal aminoalcohol on the channel properties were examined with HP-A-I, HP-A-V and HP-A-Pheol, whose C-termini are leucinol (Leuol), isoleucinol (Ileol) and phenylalaninol (Pheol), respectively. The substitution of Pheol for Leuol and Ileol prolonged the open channel lifetime. A comparison of HP-A-V (Gln18) and HP-B-V (Glu18) indicated that the carboxyl group at position 18 increased both the open channel lifetime and the magnitude of unitary channel conductance at each conductance level. The pores of level 1 showed poor ion-selectivity for K+ over Cl-. The selectivity order of alkali metal cations was Rb > or = Cs > or = K > Na > Li for level 1 and Cs > Rb > K > Na > Li for level 0. The unitary current-voltage characteristics showed non-linear relationships, which were simulated by a Nernst-Planck approach with a simple barrier model.
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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 ╳
