A-72363 A2

A-72363 A2

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Category Enzyme inhibitors
Catalog number BBF-03164
CAS
Molecular Weight 218.21
Molecular Formula C8H14N2O5

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Description

A-72363 A2 is a Heparanase inhibitor produced by Streptomyces nobilis SANK 60192.

Specification

Synonyms A-72363 A-2; 4beta,5beta-Dihydroxy-6beta-(acetylamino)piperidine-3alpha-carboxylic acid
IUPAC Name (3S,4R,5S,6R)-6-acetamido-4,5-dihydroxypiperidine-3-carboxylic acid
Canonical SMILES CC(=O)NC1C(C(C(CN1)C(=O)O)O)O
InChI InChI=1S/C8H14N2O5/c1-3(11)10-7-6(13)5(12)4(2-9-7)8(14)15/h4-7,9,12-13H,2H2,1H3,(H,10,11)(H,14,15)/t4-,5+,6+,7+/m0/s1
InChI Key DQTKLICLJUKNCG-BDVNFPICSA-N

Properties

Appearance White Powder
Boiling Point 579.2±50.0°C at 760 mmHg
Density 1.5±0.1 g/cm3
Solubility Soluble in Water

Reference Reading

1. A-72363 A-1, A-2 and C, novel heparanase inhibitors from Streptomyces nobilis SANK 60192. I. Taxonomy of producing organism, fermentation, isolation and structure elucidation
T Takatsu, M Takahashi, Y Kawase, R Enokita, T Okazaki, H Matsukawa, K Ogawa, Y Sakaida, T Kagasaki, T Kinoshita, M Nakajima, K Tanzawa J Antibiot (Tokyo). 1996 Jan;49(1):54-60. doi: 10.7164/antibiotics.49.54.
Novel heparanse inhibitors, A72363 A-1, A-2, and C, were isolated from the culture filtrate of Streptomyces nobilis SANK 60192 by column chromatography on various resinous adsorbents, followed by preparative anion exchange HPLC. Spectroscopic studies revealed that they are diastereomers of siastatin B, a neuraminidase inhibitor.
2. A-72363 A-1, A-2, and C, novel heparanase inhibitors from Streptomyces nobilis SANK 60192, II. Biological activities
Y Kawase, M Takahashi, T Takatsu, M Arai, M Nakajima, K Tanzawa J Antibiot (Tokyo). 1996 Jan;49(1):61-4. doi: 10.7164/antibiotics.49.61.
Inhibitory activities of A-72363 A-1, A-2 and C, the diastereomers of a neuraminidase inhibitor siastatin B, against various glycosidases were tested in comparison to siastatin B. Despite these compounds differing only in their configuration, each compound showed strikingly different specificities towards the various glycosidases tested. A-72363 C inhibited bovine liver beta-glucuronidase and tumor cell heparanase with IC50 values of 1.6 microM and 12 microM, respectively.

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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