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103060-53-3

Basic Information
CAS No.: 103060-53-3
Name: Daptomycin
Molecular Structure:
Molecular Structure of 103060-53-3 (Daptomycin)
Formula: C72H101 N17 O26
Molecular Weight: 1620.67
Synonyms: Benzenebutanoic acid, N-(1-oxodecyl)-L-tryptophyl-D-asparaginyl-L-a-aspartyl-L-threonylglycyl-L-ornithyl-L-a-aspartyl-D-alanyl-L-a-aspartylglycyl-D-seryl-(3R)-3-methyl-L-a-glutamyl-a,2-diamino-g-oxo-, (13?;4)-lactone, (aS)-;Cidecin;Cubicin;Dapcin;Daptomicina;Daptomycine;Daptomycinum;Deptomycin;LY 146032;N-(1-Oxodecyl)-L-tryptophyl-D-asparaginyl-L-a-aspartyl-L-threonylglycyl-L-ornithyl-L-a-aspartyl-D-alanyl-L-a-aspartylglycyl-D-seryl-(3R)-3-methyl-L-a-glutamyl-(aS)-a,2-diamino-g-oxobenzenebutanoicacid (13?;
EINECS: 600-389-2
Density: 1.45 g/cm3
Melting Point: 202-204?C
Boiling Point: 2078.2 °C at 760 mmHg
Flash Point: 1210.7 °C
Solubility:
Appearance: White powder
Hazard Symbols:
Risk Codes:
Safety:
Transport Information:
PSA: 702.02000
LogP: 0.88280
Synthetic route
334-48-5

1-decanoic acid

29022-11-5

N-(fluoren-9-ylmethoxycarbonyl)glycine

1429504-34-6

(2S,3R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-3-methyl-5-oxopentanoic acid

C23H20N4O3

C62H58N4O15

35661-38-2, 35661-39-3, 79990-15-1

N-(9-fluorenylmethoxycarbonyl)-D-alanine

73731-37-0

Fmoc-Thr-OH

73724-45-5, 136083-72-2, 116861-26-8

(R)-N-(fluoren-9-ylmethoxycarbonyl)serine

109425-55-0

Fmoc-Orn(Boc)-OH

88223-98-7

p-toluenesulfonic acid salt of glycine allyl ester

144120-53-6

(S)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(allyloxy)-4-oxobutanoic acid

144120-52-5

4-(1,1-dimethylethyl) ester of Nα-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-aspartic acid allyl ester

333366-23-7

(S)-(−)-4-tert-butyl 2-azidosuccinic acid

(S)-2-azido-3-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)propanoic acid

103060-53-3

daptomycin

Conditions
ConditionsYield
Stage #1: (S)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(allyloxy)-4-oxobutanoic acid With N-ethyl-N,N-diisopropylamine In dichloromethane for 4h; 2-chlorotrityl chloride resin;
Stage #2: With tetrakis(triphenylphosphine) palladium(0); 1,3-dimethylbarbituric acid In dichloromethane; N,N-dimethyl-formamide for 1h; 2-chlorotrityl chloride resin;
Stage #3: 1-decanoic acid; N-(fluoren-9-ylmethoxycarbonyl)glycine; (2S,3R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-3-methyl-5-oxopentanoic acid; C23H20N4O3; C62H58N4O15; N-(9-fluorenylmethoxycarbonyl)-D-alanine; Fmoc-Thr-OH; (R)-N-(fluoren-9-ylmethoxycarbonyl)serine; Fmoc-Orn(Boc)-OH; p-toluenesulfonic acid salt of glycine allyl ester; 4-(1,1-dimethylethyl) ester of Nα-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-aspartic acid allyl ester; (S)-(−)-4-tert-butyl 2-azidosuccinic acid; (S)-2-azido-3-(1-(tert-butoxycarbonyl)-1H-indol-3-yl)propanoic acid Further stages;
9%

dimethylallyl pyrophosphate

dimethylallyl pyrophosphate

C77H109N17O26

Conditions
ConditionsYield
In aq. buffer at 37℃; for 12h; pH=8;60%
103060-53-3

daptomycin

C82H102N6O16

C153H199N23O42

Conditions
ConditionsYield
Stage #1: C82H102N6O16 With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at 0℃; for 1h;
Stage #2: daptomycin With sodium hydrogencarbonate In tetrahydrofuran; water at 0 - 20℃;
48%
159857-81-5

N-[6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoyl]-L-valyl-N5-carbamoyl-N[4-({[(4-nitrophenoxy)carbonyl]oxy}methyl)phenyl]-L-ornithinamide

103060-53-3

daptomycin

MC-vc-PAB-daptomycin

Conditions
ConditionsYield
With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Sealed tube;44%
103060-53-3

daptomycin

C24H25N3O9

C92H121N19O33

Conditions
ConditionsYield
With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 20h;37%
103060-53-3

daptomycin

22679-02-3

dimethylallyl pyrophosphate

C77H109N17O26

C77H109N17O26

Conditions
ConditionsYield
In aq. buffer at 37℃; for 12h; pH=8;6%
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History

 Daptomycin (CAS NO.103060-53-3) was originally discovered by researchers at Eli Lilly and Company in the 1980s, who designated the compound LY 146032. It showed promise in Phase I/II clinical trials for the treatment of infections caused by Gram-positive organisms. However, high dose therapy was found to be associated with adverse effects on skeletal muscle, including myalgia and the potential for myositis, and Lilly ceased development. The rights to LY 146032 were subsequently acquired by Cubist Pharmaceuticals in 1997. Food and Drug Administration (FDA) approval in September 2003. Daptomycin is marketed in the EU and several other countries by Novartis following its buying of Chiron Corporation. Outside of the US, Daptomycin is available in Canada and many European countries, with further launches expected in 2008.

Specification

1. Introduction of Daptomycin

Daptomycin is one kind of white crystalline powder, odorless, little bitter taste. If you want to keep it, it should be stored in cool and dry places, keep away from light. Besids, this chemical belongs to the Product Category which include Antibacterial; Intermediates & Fine Chemicals; Pharmaceuticals. In addition, Daptomycin is a naturally-occurring compound found in the soil saprotroph Streptomyces roseosporus.

2. Properties of Daptomycin

Daptomycin has the following property datas: (1)Density: 1.45 g/cm3; (2)Index of Refraction: 1.638; (3)Flash Point: 1210.7 °C; (4)Enthalpy of Vaporization: 366.93 kJ/mol; (5)Boiling Point: 2078.2 °C at 760 mmHg.

3. Structure Descriptors of Daptomycin

You could convert the following datas into the molecular structure:
(1). InChI: 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 
(2). InChIKey: InChIKey=DOAKLVKFURWEDJ-OFNKPWESSA-N
(3). Smiles: C(=O)(N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)NC1C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@@H](CC(=O)O)C(=O)NCC(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)OC1C)CC(=O)c1ccccc1N)[C@@H](CC(=O)O)C)CO)C)CC(=O)O)CCCN)CC(=O)O)CC(=O)N)Cc1c[nH]c2c1cccc2)CCCCCCCCC

4. Use of Daptomycin

Daptomycin is a novel lipopeptide antibiotic used in the treatment of certain infections caused by Gram-positive organisms. Its distinct mechanism of action means that it may be useful in treating infections caused by multi-resistant bacteria.

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