Journal
BIOORGANIC & MEDICINAL CHEMISTRY
Volume 26, Issue 23-24, Pages 6050-6055Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2018.11.007
Keywords
Genome mining; Lasso peptide; NMR spectrum; Anti-HIV activity
Funding
- Japan Society for the Promotion of Science [16K01913]
- Nagase Science and Technology Foundation
- Sasakawa Scientific Research Grant from The Japan Science Society [2018-3001]
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Based on genome mining, a new lasso peptide specialicin was isolated from the extract of Streptomyces specialis. The structure of specialicin was established by ESI-MS and NMR analyses to be a lasso peptide with the length of 21 amino acids, containing an isopeptide bond and two disulfide bonds in the molecule. The stereochemistries of the constituent amino acids except for Trp were determined to be L and the stereochemistry of Trp at C-terminus was determined to be D. Three dimensional structure of specialicin was determined based on NOE experimental data, which indicated that specialicin possessed the similar conformational structure with siamycin I. Specialicin showed the antibacterial activity against Micrococcus luteus and the moderate anti-HIV activity against HIV-1 NL4-3. The biosynthetic gene cluster of specialicin was proposed from the genome sequence data of S. specialis.
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