Benarthin

Benarthin

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Benarthin
Category Enzyme inhibitors
Catalog number BBF-00281
CAS 143651-45-0
Molecular Weight 411.41
Molecular Formula C17H25N5O7

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Description

Benarthin is produced by the strain of Streptomyces xanthophaeus MJ 244-SF1. It inhibited the activity of pyroglutaminase and competed with the substrate, and the inhibitory constant Ki and Km was 1.2x10-6 mol/L and 3.3x10-5 mol/L, respectively.

Specification

Synonyms N-(N(sup 2)-(2,3-Dihydroxybenzoyl)-L-arginyl)-L-threonine; L-Threonine, N-(N2-(2,3-dihydroxybenzoyl)-L-arginyl)-
IUPAC Name (2S,3R)-2-[[(2S)-5-(diaminomethylideneamino)-2-[(2,3-dihydroxybenzoyl)amino]pentanoyl]amino]-3-hydroxybutanoic acid
Canonical SMILES CC(C(C(=O)O)NC(=O)C(CCCN=C(N)N)NC(=O)C1=C(C(=CC=C1)O)O)O
InChI InChI=1S/C17H25N5O7/c1-8(23)12(16(28)29)22-15(27)10(5-3-7-20-17(18)19)21-14(26)9-4-2-6-11(24)13(9)25/h2,4,6,8,10,12,23-25H,3,5,7H2,1H3,(H,21,26)(H,22,27)(H,28,29)(H4,18,19,20)/t8-,10+,12+/m1/s1
InChI Key RYFDAFYFFUVLNW-QRTLGDNMSA-N

Properties

Appearance Colorless Powder
Melting Point 178-180 °C
Solubility Soluble in water, methanol, insoluble in chloroform, ethyl acetate and hexane.

Reference Reading

1. Multi-omics Study of Planobispora rosea, Producer of the Thiopeptide Antibiotic GE2270A
Francesco Del Carratore, Marianna Iorio, Mercedes Pérez-Bonilla, Kamila Schmidt, Rosario Pérez-Redondo, Margherita Sosio, Sandy J Macdonald, Ivan S Gyulev, Areti Tsigkinopoulou, Gavin H Thomas, Olga Genilloud, Antonio Rodríguez-García, Stefano Donadio, Rainer Breitling, Eriko Takano mSystems. 2021 Jun 29;6(3):e0034121. doi: 10.1128/mSystems.00341-21. Epub 2021 Jun 22.
Planobispora rosea is the natural producer of the potent thiopeptide antibiotic GE2270A. Here, we present the results of a metabolomics and transcriptomics analysis of P. rosea during production of GE2270A. The data generated provides useful insights into the biology of this genetically intractable bacterium. We characterize the details of the shutdown of protein biosynthesis and the respiratory chain associated with the end of the exponential growth phase. We also provide the first description of the phosphate regulon in P. rosea. Based on the transcriptomics data, we show that both phosphate and iron are limiting P. rosea growth in our experimental conditions. Additionally, we identified and validated a new biosynthetic gene cluster associated with the production of the siderophores benarthin and dibenarthin in P. rosea. Together, the metabolomics and transcriptomics data are used to inform and refine the very first genome-scale metabolic model for P. rosea, which will be a valuable framework for the interpretation of future studies of the biology of this interesting but poorly characterized species. IMPORTANCE Planobispora rosea is a genetically intractable bacterium used for the production of GE2270A on an industrial scale. GE2270A is a potent thiopeptide antibiotic currently used as a precursor for the synthesis of two compounds under clinical studies for the treatment of Clostridium difficile infection and acne. Here, we present the very first systematic multi-omics investigation of this important bacterium, which provides a much-needed detailed picture of the dynamics of metabolism of P. rosea while producing GE2270A.
2. Streptobactin, a tricatechol-type siderophore from marine-derived Streptomyces sp. YM5-799
Yoshihide Matsuo, Kaneo Kanoh, Jae-Hyuk Jang, Kyoko Adachi, Satoru Matsuda, Osamu Miki, Toshiaki Kato, Yoshikazu Shizuri J Nat Prod. 2011 Nov 28;74(11):2371-6. doi: 10.1021/np200290j. Epub 2011 Oct 20.
A new catechol-type siderophore, streptobactin (1), was isolated from a culture broth of the marine-derived actinomycete Streptomyces sp. YM5-799. The structure of streptobactin was determined by NMR and MS analyses and ESIMS/MS experiments to be a cyclic trimer of benarthin. A dibenarthin (2), a tribenarthin (3), and benarthin (4) were also obtained. The production of 1 was regulated by an iron concentration in the culture. The iron-chelating activity of the compounds was evaluated by the chrome azurol sulfonate assay.
3. Benarthin: a new inhibitor of pyroglutamyl peptidase. III. Synthesis and structure-activity relationships
M Hatsu, M Tuda, Y Muraoka, T Aoyagi, T Takeuchi J Antibiot (Tokyo). 1992 Jul;45(7):1088-95. doi: 10.7164/antibiotics.45.1088.
Benarthin, a new inhibitor of pyroglutamyl peptidase (PG-peptidase), has been isolated from the culture filtrate of Streptomyces xanthophaeus MJ244-SF1. The structure of benarthin has been determined to be L-(2,3-dihydroxybenzoyl)arginyl-L-threonine. This structure was confirmed by the total synthesis of benarthin. Moreover, we synthesized benarthin derivatives to obtain information on the relationship between structure and inhibitory activity. The results indicated that the catechol group of benarthin is the essential moiety for the inhibition of PG-peptidase.

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