GERI-155
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| Category | Antibiotics |
| Catalog number | BBF-03581 |
| CAS | |
| Molecular Weight | 702.82 |
| Molecular Formula | C35H58O14 |
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Description
It is originally isolated from Streptomyces sp. GERI-155. GERI-155 had anti-Gram-positive bacteria (MIC 0.09-12.5 μg/mL) and some Gram-negative bacteria, such as Pseudomonas aeruginosa and Salmonella typhimurium activities.
Specification
| IUPAC Name | (1S,2R,3R,6E,8S,9S,10S,12S,16R)-12-hydroxy-2-[[(2R,3R,4R,5R,6R)-5-hydroxy-3,4-dimethoxy-6-methyloxan-2-yl]oxymethyl]-9-[(2S,3R,4S,6R)-3-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy-3,8,10,12-tetramethyl-4,17-dioxabicyclo[14.1.0]heptadec-6-ene-5,13-dione |
| Canonical SMILES | CC1CC(C(C(O1)OC2C(CC(C(=O)CCC3C(O3)C(C(OC(=O)C=CC2C)C)COC4C(C(C(C(O4)C)O)OC)OC)(C)O)C)O)OC |
| InChI | InChI=1S/C35H58O14/c1-17-10-13-26(37)46-20(4)22(16-44-34-32(43-9)31(42-8)27(38)21(5)47-34)30-23(48-30)11-12-25(36)35(6,40)15-18(2)29(17)49-33-28(39)24(41-7)14-19(3)45-33/h10,13,17-24,27-34,38-40H,11-12,14-16H2,1-9H3/b13-10+/t17-,18-,19+,20+,21+,22+,23+,24-,27+,28+,29+,30-,31+,32+,33-,34+,35-/m0/s1 |
| InChI Key | NMCJUPSZVLSVGC-WYHDPXJESA-N |
Properties
| Appearance | White Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Boiling Point | 818.7±65.0°C at 760 mmHg |
| Melting Point | 98.5°C |
| Density | 1.2±0.1 g/cm3 |
Reference Reading
1. Cloning, expression, and biological function of a dTDP-deoxyglucose epimerase (gerF) gene from Streptomyces sp. GERI-155
Jae-Kyung Sohng, Hyung-jun Kim, Doo-Hyun Nam, Dong-Ok Lim, Ji-Man Han, Hyo-Jung Lee, Jin-Cheol Yoo Biotechnol Lett. 2004 Feb;26(3):185-91. doi: 10.1023/b:bile.0000013709.80691.97.
GERI-155 is a macrolide antibiotic containing two deoxyhexose molecules which has antimicrobial activities against gram-positive bacteria. The deoxyhexose biosynthetic gene cluster of GERI-155 from Streptomyces sp. GERI-155 genome has now been isolated. Four orf were identified and a putative orf, supposed to code for the dTDP-deoxyglucose epimerase gene, was designated as gerF. gerF was expressed in E. coli using recombinant expression vector pHJ3. The recombinant protein expressed in a soluble form. The enzyme was purified by Ni-affinity column using imidazole buffer as eluents. The molecular mass of the expressed protein correlated with the predicted mass (36,000 Da) deduced from the cloned gene sequence data. The purified enzyme produced maltol from dTDP-4-keto-6-deoxyglucose and it was confirmed that the expressed protein was dTDP-deoxyglucose epimerase catalyzing epimerization of C-3 and C-5 or C-3 of dTDP-4-keto-6-deoxyglucose.
2. Enzymatic synthesis of dTDP-4-amino-4,6-dideoxy-D-glucose using GerB (dTDP-4-keto-6-deoxy-D-glucose aminotransferase)
Young Soo Chung, Dae Hee Kim, Won Min Seo, Hei Chan Lee, Kwangkyoung Liou, Tae-Jin Oh, Jae Kyung Sohng Carbohydr Res. 2007 Aug 13;342(11):1412-8. doi: 10.1016/j.carres.2007.04.007. Epub 2007 Apr 22.
Over-expressed GerB (dTDP-4-keto-6-deoxy-d-glucose aminotransferase) of Streptomyces sp. GERI-155 was used in the enzymatic synthesis of dTDP-4-amino-4,6-dideoxy-D-glucose (2) from dTDP-4-keto-6-deoxy-D-glucose (1). [Carbohydrate structure: see text]. Five enzymes including dTMP kinase (TMK), acetate kinase (ACK), dTDP-glucose synthase (TGS), dTDP-glucose 4,6-dehydratase (DH), and dTDP-4-keto-6-deoxy-d-glucose aminotransferase (GerB) were used to synthesize 2 on a large scale from glucose-1-phosphate and TMP. A conversion yield of up to 57% was obtained by HPLC peak integration given a reaction time of 270min. After purification by two successive preparative HPLC systems, the final product was identified by HPLC and then analyzed by (1)H, (13)C, (1)H-(1)H COSY NMR spectrometry.
3. Biosynthesis of dTDP-6-deoxy-beta-D-allose, biochemical characterization of dTDP-4-keto-6-deoxyglucose reductase (GerKI) from Streptomyces sp. KCTC 0041BP
Ta Thi Thu Thuy, Kwangkyoung Liou, Tae-jin Oh, Dea Hee Kim, Doo Hyun Nam, Jin Cheol Yoo, Jae Kyung Sohng Glycobiology. 2007 Feb;17(2):119-26. doi: 10.1093/glycob/cwl060. Epub 2006 Oct 19.
dTDP-6-deoxy-d-allose, an unusual deoxysugar, has been identified as an intermediate in the mycinose biosynthetic pathway of several macrolide antibiotics. In order to characterize the biosynthesis of this deoxysugar, we have cloned and heterologously overexpressed gerK1 in Escherichia coli BL21 (DE3) cells. This gene encodes for a protein with the putative function of a dTDP-4-keto-6-deoxyglucose reductase, which appears to be involved in the dihydrochalcomycin (GERI-155) biosynthesis evidenced by Streptomyces sp KCTC 0041BP. Our results revealed that GerK1 exhibited a specific reductive effect on the 4-keto carbon of dTDP-4-keto-6-deoxy-d-allose, with the hydroxyl group in an axial configuration at the C3 position only. The enzyme catalyzed the conversion of dTDP-4-keto-6-deoxyglucose to dTDP-6-deoxy-beta-D-allose, according to the results of an in vitro coupled enzyme assay, in the presence of GerF (dTDP-4-keto-6-deoxyglucose 3-epimerase). The product was isolated, and its stereochemistry was determined via nuclear magnetic resonance analysis.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
