Glycothiohexide α
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| Category | Antibiotics |
| Catalog number | BBF-01268 |
| CAS | 158446-31-2 |
| Molecular Weight | 1368.54 |
| Molecular Formula | C58H57N13O15S6 |
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Description
It is produced by the strain of Sebekia sp. LL-14E605 (NRRL 21083). It is a peptide antibiotic. It has strong activity against gram-positive bacteria including methicillin-resistant staphylococcus aureus (MRSA) and vancomycin resistant enterococcus (VREF), MIC is 0.03-0.06 μg/mL.
Specification
| Synonyms | Antibiotic LL 14E605α; Glycothiohexide alpha |
| IUPAC Name | 2-[(1S,18S,21E,29S,30R)-30-[(2S,4S,5R,6S)-5-(dimethylamino)-4-hydroxy-4,6-dimethyloxan-2-yl]oxy-9-hydroxy-18-[(1R)-1-hydroxyethyl]-21-(1-methoxyethylidene)-16,19,26,31,42,46-hexaoxo-32,54-dioxa-3,13,23,43,49-pentathia-7,17,20,27,45,51,52,55,56,57-decazadecacyclo[26.16.6.229,40.12,5.112,15.122,25.138,41.147,50.06,11.034,39]heptapentaconta-2(57),4,6,8,10,12(56),14,22(55),24,34(39),35,37,40,47,50-pentadecaen-8-yl]-1,3-thiazole-4-carboxamide |
| Canonical SMILES | CC1C(C(CC(O1)OC2C3C4C5=NC(=CS5)C(=O)NC(CSC(=O)C6=C(CO3)C7=C(COC2=O)C=CC=C7N6)C8=NC(=CS8)C9=NC(=C(C=C9C1=NC(=CS1)C(=O)NC(C(=O)NC(=C(C)OC)C1=NC(=CS1)C(=O)N4)C(C)O)O)C1=NC(=CS1)C(=O)N)(C)O)N(C)C |
| InChI | InChI=1S/C58H57N13O15S6/c1-21(72)37-50(78)69-38(22(2)82-7)53-65-32(19-90-53)49(77)70-42-43-44(86-35-12-58(4,81)45(71(5)6)23(3)85-35)56(79)84-13-24-9-8-10-27-36(24)26(14-83-43)40(60-27)57(80)92-20-33(61-47(75)30-18-91-55(42)66-30)52-62-28(15-88-52)39-25(51-64-31(17-87-51)48(76)68-37)11-34(73)41(67-39)54-63-29(16-89-54)46(59)74/h8-11,15-19,21,23,33,35,37,42-45,60,72-73,81H,12-14,20H2,1-7H3,(H2,59,74)(H,61,75)(H,68,76)(H,69,78)(H,70,77)/b38-22+/t21-,23+,33+,35+,37+,42?,43+,44-,45-,58+/m1/s1 |
| InChI Key | SQNIUXZFYJCFRU-XOKPMMODSA-N |
Properties
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Solubility | Soluble in Methanol |
Reference Reading
1. Potent Antibiotic Lemonomycin: A Glimpse of Its Discovery, Origin, and Chemical Synthesis
Shunan Tao, Yang Wang, Ran Hong, Sha-Hua Huang Molecules. 2022 Jul 5;27(13):4324. doi: 10.3390/molecules27134324.
Lemonomycin (1) was first isolated from the fermentation broth of Streptomyces candidus in 1964. The complete chemical structure was not elucidated until 2000 with extensive spectroscopic analysis. Lemonomycin is currently known as the only glycosylated tetrahydroisoquinoline antibiotic. Its potent antibacterial activity against Staphylococcus aureus and Bacillus subtilis and complex architecture make it an ideal target for total synthesis. In this short review, we summarize the research status of lemonomycin for biological activity, biosynthesis, and chemical synthesis. The unique deoxy aminosugar-lemonose was proposed to play a crucial role in biological activity, as shown in other antibiotics, such as arimetamycin A, nocathiacin I, glycothiohexide α, and thiazamycins. Given the self-resistance of the original bacterial host, the integration of biosynthesis and chemical synthesis to pursue efficient synthesis and further derivatization is in high demand for the development of novel antibiotics to combat antibiotic-resistant infections.
2. Importance of Noncovalent Interactions Involving Sulfur Atoms in Thiopeptide Antibiotics-Glycothiohexide α and Nocathiacin I
Volga Kojasoy, Dean J Tantillo J Phys Chem A. 2023 Feb 28. doi: 10.1021/acs.jpca.2c07600. Online ahead of print.
Noncovalent interactions involving sulfur atoms play essential roles in protein structure and function by significantly contributing to protein stability, folding, and biological activity. Sulfur is a highly polarizable atom that can participate in many types of noncovalent interactions including hydrogen bonding, sulfur-π interactions, and S-lone pair interactions, but the impact of these sulfur-based interactions on molecular recognition and drug design is still often underappreciated. Here, we examine, using quantum chemical calculations, the roles of sulfur-based noncovalent interactions in complex naturally occurring molecules representative of thiopeptide antibiotics: glycothiohexide α and its close structural analogue nocathiacin I. While donor-acceptor orbital interactions make only very small contributions, electrostatic and dispersion contributions are predicted to be significant in many cases. In pursuit of understanding the magnitudes and nature of these noncovalent interactions, we made potential structural modifications that could significantly expand the chemical space of effective thiopeptide antibiotics.
3. Chemical conversion of nocathiacin I to nocathiacin II and a lactone analogue of glycothiohexide alpha
Timothy P Connolly, Alicia Regueiro-Ren, John E Leet, Dane M Springer, Jason Goodrich, Xiaohua Stella Huang, Michael J Pucci, Junius M Clark, Joanne J Bronson, Yasutsugu Ueda J Nat Prod. 2005 Apr;68(4):550-3. doi: 10.1021/np040225d.
Nocathiacin I (1) was converted to its deoxy indole analogue, nocathiacin II (2), another natural product, by a unique and facile chemical process. This process was applied to nocathiacin IV (4), generating the lactone analogue of glycothiohexide alpha (5), which was also prepared from nocathiacin II by a mild hydrolytic process. In contrast to glycothiohexide alpha (3), this lactone analogue (5) was found to exhibit in vivo antibacterial efficacy in an animal (mouse) infection 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 ╳
