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L-681176

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L-681176
Category Enzyme inhibitors
Catalog number BBF-03613
CAS 91386-17-3
Molecular Weight 349.34
Molecular Formula C12H23N5O7

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Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

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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

L-681176 is originally isolated from Streptomyces sp. MA 5143a. It has the activity of inhibiting angiotensin transferase.

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Synonyms L-681,176
IUPAC Name 2-[2-[[1-carboxy-4-(diaminomethylideneamino)-3-hydroxybutyl]amino]ethylamino]butanedioic acid
Canonical SMILES C(CNC(CC(=O)O)C(=O)O)NC(CC(CN=C(N)N)O)C(=O)O
InChI InChI=1S/C12H23N5O7/c13-12(14)17-5-6(18)3-7(10(21)22)15-1-2-16-8(11(23)24)4-9(19)20/h6-8,15-16,18H,1-5H2,(H,19,20)(H,21,22)(H,23,24)(H4,13,14,17)
InChI Key UULSZYUKAFTXQP-UHFFFAOYSA-N
Appearance Colorless Acicular Crystal
Boiling Point 690.9°C at 760 mmHg
Density 1.62 g/cm3
1. Discovery, purification and characterization of the angiotensin converting enzyme inhibitor, L-681,176, produced by Streptomyces sp. MA 5143a
L Huang, G Rowin, J Dunn, R Sykes, R Dobna, B A Mayles, D M Gross, R W Burg J Antibiot (Tokyo). 1984 May;37(5):462-5. doi: 10.7164/antibiotics.37.462.
L-681,176, an inhibitor of angiotensin converting enzyme was found in the culture filtrate of Streptomyces sp. MA 5143. The I50 of the crystalline inhibitor is about 1.3 micrograms/ml and the inhibition is reversed by zinc sulfate. In rats, L-681,176 exhibits a dose-related inhibition of the pressor response to angiotensin I with an ID50 of 142 mg/kg when administered intravenously. The structure of L-681,176 is similar to that of marasmine but lacking one carboxyl group. The maximum yield of L-681,176 occurs after three to four days growth at 28 degrees C.
2. Structure elucidation of angiotensin converting enzyme inhibitor L-681,176 from Streptomyces sp. MA 5143a
O D Hensens, J M Liesch J Antibiot (Tokyo). 1984 May;37(5):466-8. doi: 10.7164/antibiotics.37.466.
L-681,176 (1, C12H23N5O7) is an inhibitor of angiotensin converting enzyme produced by Streptomyces sp. MA 5143a. The structure of L-681,176 has been determined by NMR and mass spectral analysis.

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