Propeptin
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| Category | Antibiotics |
| Catalog number | BBF-02066 |
| CAS | |
| Molecular Weight | 2296.49 |
| Molecular Formula | C113H142N26O27 |
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Description
Propeptin is a metabolite of Microbispora sp. SNA 115, a peptide antibiotic composed of 19 amino acids. Propeptin has weaker activity against Pseudomonas aeruginosa, Mycobacterium monobacterium, and Xanthomonas oryzae. It has no effect on KB and L1210 cells of tumor cell lines, but has an inhibitory effect on prolyl endopeptidase.
Specification
| IUPAC Name | 1-[2-[[2-[[2-[[2-[[2-[[2-[[2-[[2-[[2-[[13-(3-carbamimidamidopropyl)-19-(carboxymethyl)-3,16-bis[(4-hydroxyphenyl)methyl]-22,25-bis(1H-indol-3-ylmethyl)-2,5,8,12,15,18,21,24,27-nonaoxo-1,4,7,11,14,17,20,23,26-nonazabicyclo[26.3.0]hentriacontane-10-carbonyl]amino]-4-methylpentanoyl]amino]-3-phenylpropanoyl]amino]acetyl]amino]acetyl]amino]-3-(1H-imidazol-4-yl)propanoyl]amino]-3-hydroxybutanoyl]amino]-3-phenylpropanoyl]amino]-3-methylpentanoyl]amino]-3-hydroxypropanoyl]pyrrolidine-2-carboxylic acid |
| Canonical SMILES | CCC(C)C(C(=O)NC(CO)C(=O)N1CCCC1C(=O)O)NC(=O)C(CC2=CC=CC=C2)NC(=O)C(C(C)O)NC(=O)C(CC3=CNC=N3)NC(=O)CNC(=O)CNC(=O)C(CC4=CC=CC=C4)NC(=O)C(CC(C)C)NC(=O)C5CC(=O)NCC(=O)NC(C(=O)N6CCCC6C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N5)CCCNC(=N)N)CC7=CC=C(C=C7)O)CC(=O)O)CC8=CNC9=CC=CC=C98)CC1=CNC2=CC=CC=C21)CC1=CC=C(C=C1)O |
| InChI | InChI=1S/C113H142N26O27/c1-6-61(4)95(108(161)135-87(58-140)111(164)139-41-19-30-89(139)112(165)166)136-105(158)80(44-64-22-11-8-12-23-64)134-109(162)96(62(5)141)137-106(159)83(49-69-54-116-59-123-69)124-92(146)57-121-91(145)55-122-97(150)78(43-63-20-9-7-10-21-63)128-99(152)77(42-60(2)3)127-103(156)84-50-90(144)120-56-93(147)125-86(46-66-33-37-71(143)38-34-66)110(163)138-40-18-29-88(138)107(160)133-82(48-68-53-119-75-27-16-14-25-73(68)75)102(155)130-81(47-67-52-118-74-26-15-13-24-72(67)74)101(154)132-85(51-94(148)149)104(157)129-79(45-65-31-35-70(142)36-32-65)100(153)126-76(98(151)131-84)28-17-39-117-113(114)115/h7-16,20-27,31-38,52-54,59-62,76-89,95-96,118-119,140-143H,6,17-19,28-30,39-51,55-58H2,1-5H3,(H,116,123)(H,120,144)(H,121,145)(H,122,150)(H,124,146)(H,125,147)(H,126,153)(H,127,156)(H,128,152)(H,129,157)(H,130,155)(H,131,151)(H,132,154)(H,133,160)(H,134,162)(H,135,161)(H,136,158)(H,137,159)(H,148,149)(H,165,166)(H4,114,115,117) |
| InChI Key | VIRBPQIAVNKZST-UHFFFAOYSA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | Gram-negative bacteria |
| Melting Point | 230-240°C (dec.) |
| Density | 1.5±0.1 g/cm3 |
Reference Reading
1. Propeptin, a new inhibitor of prolyl endopeptidase produced by microbispora II. Determination of chemical structure
Yasuaki Esumi, Yoshikatsu Suzuki, Yumiko Itoh, Masakazu Uramoto, Ken-ichi Kimura, Masaaki Goto, Makoto Yoshihama, Teruo Ichikawa J Antibiot (Tokyo). 2002 Mar;55(3):296-300. doi: 10.7164/antibiotics.55.296.
The structure of propeptin, a new inhibitor of prolyl endopeptidase isolated from Microbispora sp. SNA-115, was determined. FAB/MS, Edman degradation and amino acid analysis revealed propeptin to be a cyclic polypeptide consisting of 19 common L-amino acids. By FAB/MS and protein chemical methods, the primary sequence of propeptin was determined to be Gly1-Tyr-Pro-Trp-Trp-Asp-Tyr-Arg-Asp9-Leu-Phe-Gly-Gly-His-Thr-Phe-Ile-Ser-Pro19, which cyclizes between the beta-carboxyl group of Asp9 and the a-amino group of Gly1.
2. Novel propeptin analog, propeptin-2, missing two amino acid residues from the propeptin C-terminus loses antibiotic potency
Ken-ichi Kimura, Mai Yamazaki, Noriko Sasaki, Tetsuro Yamashita, Shigenori Negishi, Takemichi Nakamura, Hiroyuki Koshino J Antibiot (Tokyo). 2007 Aug;60(8):519-23. doi: 10.1038/ja.2007.66.
A novel inhibitor of prolyl endopeptidase, the propeptin analog propeptin-2 (C105H130N24O(24)), missing two amino acid residues from the propeptin C-terminus was isolated from the fermentation broth of propeptin-producing Microbispora sp. SNA-115 grown using a large inoculum. It shows the same enzyme inhibition activity as propeptin against prolyl endopeptidase (Ki=1.5 microM), but its antimicrobial activity against Mycobacterium phlei is more than 100-fold lower.
3. Anti-Mycobacterium activity of microbial peptides in a silkworm infection model with Mycobacterium smegmatis
Akiho Yagi, Ryuji Uchida, Hiroshi Hamamoto, Kazuhisa Sekimizu, Ken-Ichi Kimura, Hiroshi Tomoda J Antibiot (Tokyo). 2017 May;70(5):685-690. doi: 10.1038/ja.2017.23.
An in vivo-mimic silkworm infection model with Mycobacterium smegmatis was established. When silkworms were raised at 37 °C following an injection of M. smegmatis cells (1.25 × 107 CFU larva-1 g-1) into the silkworm hemolymph, they died within 48 h. Under these conditions, four microbial peptides with anti-M. smegmatis activity, lariatin A, calpinactam, lysocin E and propeptin, exerted therapeutic effects in a dose-dependent manner, and these are also clinically used agents that are active against Mycobacterium tuberculosis. These results indicate that the silkworm infection model with M. smegmatis is practically useful for the screening of therapeutically effective anti-M. tuberculosis antibiotics.
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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 ╳
