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TMC-2C

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Category Enzyme inhibitors
Catalog number BBF-02521
CAS
Molecular Weight 554.6
Molecular Formula C28H34N4O8

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Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

TMC-2C is a dipeptidyl peptidase IV (DPIV) inhibitor isolated from the fermentation broth of Aspergillus oryzae A374. It inhibited rat kidney DPIV with IC50 value of 8.1 μmol/L.

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Synonyms TMC-2 C
IUPAC Name (2S,4S)-2-[[(3S)-2-[(2S)-2-amino-3-(1H-indol-3-yl)propanoyl]-6,8-dihydroxy-7-methoxy-3,4-dihydro-1H-isoquinoline-3-carbonyl]amino]-5-hydroxy-4-methylpentanoic acid
Canonical SMILES CC(CC(C(=O)O)NC(=O)C1CC2=CC(=C(C(=C2CN1C(=O)C(CC3=CNC4=CC=CC=C43)N)O)OC)O)CO
InChI InChI=1S/C28H34N4O8/c1-14(13-33)7-21(28(38)39)31-26(36)22-9-15-10-23(34)25(40-2)24(35)18(15)12-32(22)27(37)19(29)8-16-11-30-20-6-4-3-5-17(16)20/h3-6,10-11,14,19,21-22,30,33-35H,7-9,12-13,29H2,1-2H3,(H,31,36)(H,38,39)/t14-,19-,21-,22-/m0/s1
InChI Key WVYIXBYYAHYOIW-GLYDZZHWSA-N
Appearance White Powder
Melting Point 175-181°C (dec.)
1. TMC-2A, -2B and -2C, new dipeptidyl peptidase IV inhibitors produced by Aspergillus oryzae A374. II. Isolation and structure determination
Y Asai, N Nonaka, M Nishio, K Okamura, T Date, T Sugita, T Ohnuki, S Komatsubara J Antibiot (Tokyo). 1997 Aug;50(8):653-8. doi: 10.7164/antibiotics.50.653.
New dipeptidyl peptidase IV inhibitors, TMC-2A, -2B, and -2C, were isolated from the fermentation broth of Aspergillus oryzae A374. On the basis of chemical, spectroscopic and X-ray crystallographic analyses, their structures were established to be peptide-like compounds composed of three moieties, L-tryptophan, mono- or dihydroxy-L-leucine and highly substituted isoquinoline.
2. TMC-2A, -2B and -2C, novel dipeptidyl peptidase IV inhibitors produced by Aspergillus oryzae A374. I. Taxonomy of producing strain, fermentation, and biochemical properties
N Nonaka, Y Asai, M Nishio, K Takahashi, T Okuda, S Tanaka, T Sugita, T Ohnuki, S Komatsubara J Antibiot (Tokyo). 1997 Aug;50(8):646-52. doi: 10.7164/antibiotics.50.646.
TMC-2A(1), -2B (2) and -2C (3), novel dipeptidyl peptidase IV (DPIV) inhibitors, were isolated from the fermentation broth of Aspergillus oryzae A374. TMC-2A, -2B and -2C inhibited rat kidney DPIV with IC50 value of 8.1 microM, 17 microM, and 20 microM, respectively, as well as human DPIV prepared from mononuclear cells and adenocarcinoma cells. TMC-2 compounds inhibited only DPIV among the proteases tested, indicating their high selectivity for DPIV. The kinetic analyses revealed that TMC-2A was an uncompetitive inhibitor. Taxonomy and fermentation of the producing strain are also described.

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