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Streptocidin B

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Category Bioactive by-products
Catalog number BBF-03064
CAS
Molecular Weight 1298.53
Molecular Formula C67H91N15O12

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Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

Streptocidin B is a cyclic decapeptide produced by Streptomyces sp. Tu 6071.

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IUPAC Name 3-[(3R,6S,9S,12S,15S,18S,21S,24R,27S,30S)-21-(2-amino-2-oxoethyl)-9-(3-aminopropyl)-3-benzyl-15,24-bis(1H-indol-3-ylmethyl)-6,27-bis(2-methylpropyl)-2,5,8,11,14,17,20,23,26,29-decaoxo-12-propan-2-yl-1,4,7,10,13,16,19,22,25,28-decazabicyclo[28.3.0]tritriacontan-18-yl]propanamide
Canonical SMILES CC(C)CC1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N2CCCC2C(=O)N1)CC3=CC=CC=C3)CC(C)C)CCCN)C(C)C)CC4=CNC5=CC=CC=C54)CCC(=O)N)CC(=O)N)CC6=CNC7=CC=CC=C76
InChI InChI=1S/C67H91N15O12/c1-36(2)28-48-61(88)80-53(30-39-16-8-7-9-17-39)67(94)82-27-15-23-54(82)65(92)79-49(29-37(3)4)60(87)77-50(31-40-34-71-44-20-12-10-18-42(40)44)62(89)78-52(33-56(70)84)63(90)73-47(24-25-55(69)83)59(86)76-51(32-41-35-72-45-21-13-11-19-43(41)45)64(91)81-57(38(5)6)66(93)74-46(22-14-26-68)58(85)75-48/h7-13,16-21,34-38,46-54,57,71-72H,14-15,22-33,68H2,1-6H3,(H2,69,83)(H2,70,84)(H,73,90)(H,74,93)(H,75,85)(H,76,86)(H,77,87)(H,78,89)(H,79,92)(H,80,88)(H,81,91)/t46-,47-,48-,49-,50+,51-,52-,53+,54-,57-/m0/s1
InChI Key AQJHOZTVIQPXMD-VUJDHBQASA-N
Boiling Point 1673.1±65.0°C at 760 mmHg
Density 1.3±0.1 g/cm3
1. Streptocidins A-D, novel cyclic decapeptide antibiotics produced by Streptomyces sp. Tü 6071. II. Structure elucidation
A Höltzel, R W Jack, G J Nicholson, G Jung, K Gebhardt, H P Fiedler, R D Süssmuth J Antibiot (Tokyo). 2001 May;54(5):434-40. doi: 10.7164/antibiotics.54.434.
The structures of the new antibiotics streptocidins A approximately D were elucidated as cyclic decapeptides cyclo[L-Val1-L-Orn2-L-Leu3-D-Phe4-L-Pro5-L-Leu6-X7-L-Asn8-L-Gln9-X10] with X7=D-Trp (A, B, C) or D-Phe (D) and X10=L-Tyr (A), L-Trp (B, D), or D-Trp (C). The amino acid composition (including the configuration) of the substances was determined by chiral-phase GC-MS of the hydrolysates. The sequences were established by EDMAN degradation following linearisation of the cyclic peptides upon treatment with LiAlH4. NMR spectroscopic studies of streptocidins C and D confirmed the proposed sequences and provided conformational data which indicate a molecular topology of streptocidins C and D similar to those of tyrocidine A and gramicidin S.
2. Streptocidins A-D, novel cyclic decapeptide antibiotics produced by Streptomyces sp. Tü 6071. I. Taxonomy, fermentation, isolation and biological activities
K Gebhardt, R Pukall, H P Fiedler J Antibiot (Tokyo). 2001 May;54(5):428-33. doi: 10.7164/antibiotics.54.428.
Four novel cyclic homodecapetide antibiotics, streptocidins A-D were detected in the mycelium extract of Streptomyces sp. Tü 6071 by HPLC-diode-array and HPLC-electrospray-mass-spectrometry screening. The peptides which were closely related in structure to the tyrocidines and gramicidins of Bacillus brevis show antibiotic activities against Gram-positive bacteria.

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