Napsamycin D

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Napsamycin D
Category Antibiotics
Catalog number BBF-01999
CAS 144379-27-1
Molecular Weight 868.95
Molecular Formula C40H52N8O12S

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Description

Napsamycin D is an antibiotic produced by Str.sp. HIL Y-82, 11372. It has antibacterial activity against Pseudomonas aeruginosa and other pseudomonas, but has weak antibacterial activity against other Gram-positive and negative bacteria.

Specification

Storage Store at -20°C
IUPAC Name 2-[[1-[[1-[[(Z)-[5-(2,4-dioxo-1,3-diazinan-1-yl)-4-hydroxyoxolan-2-ylidene]methyl]amino]-3-[(6-hydroxy-1-methyl-1,2,3,4-tetrahydroisoquinoline-3-carbonyl)-methylamino]-1-oxobutan-2-yl]amino]-4-methylsulfanyl-1-oxobutan-2-yl]carbamoylamino]-3-(3-hydroxyphenyl)propanoic acid
Canonical SMILES CC1C2=C(CC(N1)C(=O)N(C)C(C)C(C(=O)NC=C3CC(C(O3)N4CCC(=O)NC4=O)O)NC(=O)C(CCSC)NC(=O)NC(CC5=CC(=CC=C5)O)C(=O)O)C=C(C=C2)O
InChI InChI=1S/C40H52N8O12S/c1-20-27-9-8-25(50)16-23(27)17-29(42-20)36(55)47(3)21(2)33(35(54)41-19-26-18-31(51)37(60-26)48-12-10-32(52)45-40(48)59)46-34(53)28(11-13-61-4)43-39(58)44-30(38(56)57)15-22-6-5-7-24(49)14-22/h5-9,14,16,19-21,28-31,33,37,42,49-51H,10-13,15,17-18H2,1-4H3,(H,41,54)(H,46,53)(H,56,57)(H2,43,44,58)(H,45,52,59)/b26-19-
InChI Key AZGANZVUWUCOGH-XHPQRKPJSA-N

Properties

Appearance White Powder
Antibiotic Activity Spectrum Gram-negative bacteria
Melting Point >190°C (dec.)
Density 1.427 g/cm3
Solubility Soluble in DMSO, Methanol, Water

Reference Reading

1. Genome engineering and direct cloning of antibiotic gene clusters via phage ϕBT1 integrase-mediated site-specific recombination in Streptomyces
Deyao Du, Lu Wang, Yuqing Tian, Hao Liu, Huarong Tan, Guoqing Niu Sci Rep. 2015 Mar 4;5:8740. doi: 10.1038/srep08740.
Several strategies have been used to clone large DNA fragments directly from bacterial genome. Most of these approaches are based on different site-specific recombination systems consisting of a specialized recombinase and its target sites. In this study, a novel strategy based on phage ϕBT1 integrase-mediated site-specific recombination was developed, and used for simultaneous Streptomyces genome engineering and cloning of antibiotic gene clusters. This method has been proved successful for the cloning of actinorhodin gene cluster from Streptomyces coelicolor M145, napsamycin gene cluster and daptomycin gene cluster from Streptomyces roseosporus NRRL 15998 at a frequency higher than 80%. Furthermore, the system could be used to increase the titer of antibiotics as we demonstrated with actinorhodin and daptomycin, and it will be broadly applicable in many Streptomyces.

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It is commonly abbreviated as: C1V1 = C2V2

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