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SBR00014

Sigma-Aldrich

Daptomycin Ready Made Solution

1 mg/mL in DMSO

Synonym(s):

N-decanoyl-L-tryptophyl-L-asparaginyl-L-aspartyl-L-threonylglycyl-L-ornithyl-L-aspartyl-D-alanyl-L-aspartylglycyl-D-seryl-threo-3-methyl-L-glutamyl-3-anthraniloyl-L-alanine[egr]1-lactone

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About This Item

Empirical Formula (Hill Notation):
C72H101N17O26
CAS Number:
103060-53-3
Molecular Weight:
1620.67
MDL number:
MFCD28968054
UNSPSC Code:
51101500
NACRES:
NA.76

biological source

Streptomyces roseosporus

Quality Level

200

description

Ready Made Solution

form

liquid

storage condition

(Keep container tightly closed in a dry and well-ventilated place.)

concentration

1 mg/mL in DMSO

color

colorless to faint yellow

antibiotic activity spectrum

Gram-positive bacteria

Mode of action

DNA synthesis | interferes
protein synthesis | interferes

shipped in

dry ice

storage temp.

−20°C

SMILES string

O=C(NCC(N[C@H](CCCN)C(N[C@@H](CC(O)=O)C(N[C@H](C)C(N[C@@H](CC(O)=O)C(NC1)=O)=O)=O)=O)=O)[C@@H](NC([C@H](CC(O)=O)NC([C@@H](CC(N)=O)NC([C@H](CC2=CNC3=C2C=CC=C3)NC(CCCCCCCCC)=O)=O)=O)=O)[C@@H](C)OC([C@H](CC(C4=C(N)C=CC=C4)=O)NC([C@@]([C@H](C)CC(O)=O)([H])NC(

InChI

1S/C72H101N17O26/c1-5-6-7-8-9-10-11-22-53(93)81-44(25-38-31-76-42-20-15-13-17-39(38)42)66(108)84-45(27-52(75)92)67(109)86-48(30-59(102)103)68(110)89-61-37(4)115-72(114)49(26-51(91)40-18-12-14-19-41(40)74)87-71(113)60(35(2)24-56(96)97)88-69(111)50(34-90)82-55(95)32-77-63(105)46(28-57(98)99)83-62(104)36(3)79-65(107)47(29-58(100)101)85-64(106)43(21-16-23-73)80-54(94)33-78-70(61)112/h12-15,17-20,31,35-37,43-50,60-61,76,90H,5-11,16,21-30,32-34,73-74H2,1-4H3,(H2,75,92)(H,77,105)(H,78,112)(H,79,107)(H,80,94)(H,81,93)(H,82,95)(H,83,104)(H,84,108)(H,85,106)(H,86,109)(H,87,113)(H,88,111)(H,89,110)(H,96,97)(H,98,99)(H,100,101)(H,102,103)/t35?,36-,37?,43+,44+,45+,46+,47+,48+,49+,50-,60+,61?/m1/s1

InChI key

DOAKLVKFURWEDJ-OFNKPWESSA-N

Related Categories

Biochem/physiol Actions

Daptomycin is a natural cyclic lipopeptide antibiotic found in Streptomyces roseosporus. It is has been found to be effective in treating infections caused by aerobic Gram-positive bacteria. Daptomycin inhibits many antibiotic resistant strains such as methicillin-resistant S. aureus (MRSA), vancomycin-intermediate S. aureus (VISA) and vancomycin-resistant S. aureus (VRSA).

The mode of action of daptomycin is quite different from that of any other antibiotic. Daptomycin binds to bacterial membranes and causes a rapid depolarization of membrane potential. This loss of membrane potential causes inhibition of protein, DNA, and RNA synthesis, which results in bacterial cell death.

Packaging

0.5ML

Preparation Note

The 1 mg/mL solution may be further diluted in an appropriate buffer prior to use. It is recommended that a fresh dilution be made on the day of use.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

WGK

WGK 1

Flash Point(F)

188.6 °F

Flash Point(C)

87 °C

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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[Daptomycin: revitalizing a former drug due to the need of new active agents against grampositive multiresistant bacterias].
Hernandez Marti V, et al.
Revista Espanola de Quimioterapia : Publicacion Oficial de la Sociedad Espanola de Quimioterapia, 20, 261-276 (2007)
Reduced pulmonary surfactant interaction of daptomycin analogs via tryptophan replacement with alternative amino acids.
He Y, et al.
Bioorganic & Medicinal Chemistry Letters, 22, 6248-6251 (2012)
Feng Wang et al.
Gene, 544(2), 208-215 (2014-04-29)
Daptomycin, a novel cyclic lipopeptide antibiotic against Gram-positive bacteria, is produced by Streptomyces roseosporus. Though its biosynthetic mechanism, structural shuffling and fermentation optimization have been extensively studied, little is understood about its production regulation at the transcriptional levels. Here we
Diixa Patel et al.
International journal of antimicrobial agents, 38(5), 442-446 (2011-08-16)
Daptomycin is highly active against Staphylococcus aureus, including multidrug-resistant strains and those with reduced susceptibility to vancomycin. However, daptomycin-non-susceptible (Dap(NS)) strains [minimum inhibitory concentration (MIC) >1mg/L] have been derived clinically and in vitro. The mechanism(s) by which this occurs is

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