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R2636

Sigma-Aldrich

Rosamicin

from Micromonospora rosaria, ~98%

Synonym(s):

Juvenimicin A3, Rosaramicin

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About This Item

Empirical Formula (Hill Notation):
C31H51NO9
CAS Number:
35834-26-5
Molecular Weight:
581.74
Beilstein:
1633003
EC Number:
252-742-1
MDL number:
MFCD00133803
UNSPSC Code:
12352202
PubChem Substance ID:
24899357

biological source

Micromonospora rosaria

Assay

~98%

form

solid

storage temp.

2-8°C

SMILES string

[H]C(=O)C[C@H]1C[C@@H](C)C(=O)\C=C\[C@]2(C)O[C@@]2([H])[C@H](C)[C@@H](CC)OC(=O)C[C@@H](O)[C@H](C)[C@H]1O[C@@H]3O[C@H](C)C[C@@H]([C@H]3O)N(C)C

InChI

1S/C31H51NO9/c1-9-25-20(5)29-31(6,41-29)12-10-23(34)17(2)14-21(11-13-33)28(19(4)24(35)16-26(36)39-25)40-30-27(37)22(32(7)8)15-18(3)38-30/h10,12-13,17-22,24-25,27-30,35,37H,9,11,14-16H2,1-8H3/b12-10+/t17-,18-,19+,20-,21+,22+,24-,25-,27-,28-,29+,30+,31+/m1/s1

InChI key

IUPCWCLVECYZRV-JZMZINANSA-N

Biochem/physiol Actions

Macrolide antibiotic similar to erythromycin, and with a similar spectrum of bactericidal activity. Against a wide variety of anaerobes, rosamicin is at least as potent as, and in some cases more potent than, erythromycin.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302 + H312 + H332

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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A new Micromonospora-produced macrolide antibiotic, rosamicin.
G H Wagman et al.
The Journal of antibiotics, 25(11), 641-646 (1972-11-01)
K Funaishi et al.
The Journal of antibiotics, 43(8), 938-947 (1990-08-01)
Antibiotics 6108 A1, B, C and D, a new series of analogues of rosaramicin, were found together with rosaramicin, juvenimicin A4 and M-4365 A1 from the cultured broth of strain BA06108 which was assigned to be a new species of
Maria-José González de la Huebra et al.
Analytical and bioanalytical chemistry, 375(8), 1031-1037 (2003-05-07)
A high-performance liquid chromatography (HPLC) method using chromatographic conditions optimised in a previous work was applied for the separation of three macrolide antibiotics roxithromycin (Rox), oleandomycin (Ole) and rosamicin (Ros) and further determination of two of them, roxithromycin (Rox) and
Yohei Iizaka et al.
Antimicrobial agents and chemotherapy, 57(3), 1529-1531 (2013-01-01)
The cytochrome P450 enzyme-encoding genes rosC and rosD were cloned from the rosamicin biosynthetic gene cluster of Micromonospora rosaria IFO13697. The functions of RosC and RosD were demonstrated by gene disruption and complementation with M. rosaria and bioconversion of rosamicin
Yohei Iizaka et al.
Applied microbiology and biotechnology, 104(8), 3403-3415 (2020-02-28)
The cytochrome P450 monooxygenase RosC catalyzes the three-step oxidation reactions, which leads to the formation of a hydroxy, formyl, and carboxy group at C-20 during rosamicin biosynthesis in Micromonospora rosaria IFO13697. To determine if amino acid substitutions in RosC could
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