Taxonomic group: fungi / Mucoromycota
(Phylum: Mucoromycota)
The structure was elucidated in this paperNCBI PubMed ID: 22306315Publication DOI: 10.1016/j.jbiosc.2012.01.004Journal NLM ID: 100888800Publisher: Osaka, Japan, Amsterdam, The Netherlands: Society for Bioscience and Bioengineering
Correspondence: de Oliveira V <valeria
farmacia.ufg.br>
Institutions: Laboratório de Bioconversão, Faculdade de Farmácia, Praça Universitária, Setor Universitário, Goiânia, Brazil, Laboratório de Química Farmacêutica Medicinal, Faculdade de Farmácia, Praça Universitária, Setor Universitário, Goiânia, Brazil, Laboratório de Ressonância Magnética Nuclear, Instituto de Química, Universidade Federal de Goiás, Goiânia, Brazil
The purpose of this paper is to describe the glycosylation of entacapone by cultures of Cunninghamella echinulata ATCC 9245. This method is then applied in toxicological and pharmacological studies. The cultures were grown in a fluid PDSM medium for 7days at 28°C. After purification by silica gel flash column chromatography, the (E)-2-cyano-N,N-diethyl-3-(4-hydroxy-3-nitro-5-(3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2H-pyran-2-yloxy)phenyl) acrylamide was identified by IR, mass spectroscopy and 1H and 13C NMR. The correct position and β-configuration of the glucose was determined through HSQC, HMBC and NOE experiments.
biotransformation, Cunninghamella echinulata ATCC 9245, entacapone, entacapone glycoside, microbial glycosylation
Structure type: monomer ; 468.1 [M+H]+
Location inside paper: Fig.2
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
Methods: 13C NMR, 1H NMR, NMR-2D, IR, TLC, HPLC, extraction, column chromatography, cell growth, CLAE-EM/EM
Synthetic data: enzymatic in vivo
NCBI Taxonomy refs (TaxIDs): 76405
Show glycosyltransferases
NMR conditions: in CD3OD
[as TSV]
13C NMR data:
Linkage Residue C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12
3 bDGlcp 103.4 74.8 77.6 71.0 78.3 62.2
Subst 166.3 103.0 150.8 42.1-45.1 13.0-14.1 118.0 119.9 125.9 138.6 156.0 151.5 118.5
1H NMR data:
Linkage Residue H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12
3 bDGlcp 4.92 3.55-3.58 3.50-3.53 3.48-3.54 3.53-3.55 3.77-3.97
Subst - - 7.51 3.46-3.60 1.19-1.32 - - 8.03 - - - 8.06
1H/13C HSQC data:
Linkage Residue C1/H1 C2/H2 C3/H3 C4/H4 C5/H5 C6/H6 C7/H7 C8/H8 C9/H9 C10/H10 C11/H11 C12/H12
3 bDGlcp 103.4/4.92 74.8/3.55-3.58 77.6/3.50-3.53 71.0/3.48-3.54 78.3/3.53-3.55 62.2/3.77-3.97
Subst 150.8/7.51 42.1-45.1/3.46-3.60 13.0-14.1/1.19-1.32 125.9/8.03 118.5/8.06
1H NMR data:
| Linkage | Residue | H1 | H2 | H3 | H4 | H5 | H6 | H7 | H8 | H9 | H10 | H11 | H12 |
|---|
| 3 | bDGlcp | 4.92 | 3.55
3.58 | 3.50
3.53 | 3.48
3.54 | 3.53
3.55 | 3.77
3.97 | |
| | Subst |
|
| 7.51 | 3.46
3.60 | 1.19
1.32 |
|
| 8.03 |
|
|
| 8.06 |
|
13C NMR data:
| Linkage | Residue | C1 | C2 | C3 | C4 | C5 | C6 | C7 | C8 | C9 | C10 | C11 | C12 |
|---|
| 3 | bDGlcp | 103.4 | 74.8 | 77.6 | 71.0 | 78.3 | 62.2 | |
| | Subst | 166.3 | 103.0 | 150.8 | 42.1
45.1 | 13.0
14.1 | 118.0 | 119.9 | 125.9 | 138.6 | 156.0 | 151.5 | 118.5 |
|
There is only one chemically distinct structure:
Found 
report error