WS 1358B1

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Category Enzyme inhibitors
Catalog number BBF-01642
CAS 117703-85-2
Molecular Weight 251.1
Molecular Formula C6H7NO7Na2

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Description

WS 1358B1 is a dehydropeptide (DHP) inhibitor produced by Streptomyces parvulus.

Specification

Synonyms WS-1358B1
IUPAC Name 2-hydroxy-2-(hydroxycarbamoyl)pentanedioic acid
Canonical SMILES C(CC(C(=O)NO)(C(=O)O)O)C(=O)O
InChI InChI=1S/C6H9NO7/c8-3(9)1-2-6(13,5(11)12)4(10)7-14/h13-14H,1-2H2,(H,7,10)(H,8,9)(H,11,12)
InChI Key HUZCUQQKMFUHKG-UHFFFAOYSA-N

Properties

Melting Point 92-93°C

Reference Reading

1. Studies on new dehydropeptidase inhibitors. I. Taxonomy, fermentation, isolation and physico-chemical properties
S Hashimoto, H Murai, M Ezaki, N Morikawa, H Hatanaka, M Okuhara, M Kohsaka, H Imanaka J Antibiot (Tokyo). 1990 Jan;43(1):29-37. doi: 10.7164/antibiotics.43.29.
WS1358A1 (FR104007) and B1 (FR104008), new potent inhibitors of renal dehydropeptidase, were isolated from the culture broth of strain No. 1358 which was identified as Streptomyces parvulus subsp. In vitro inhibitory activities (IC50 value) of WS1358A1 and B1 against porcine renal DHP were 3 and 600 nM, respectively.
2. Studies on new dehydropeptidase inhibitors. IV. Chemical transformation of WS1358 compounds and an improved synthesis of WS1358A1
I Uchida, S Hashimoto, T Iwamoto, S Takase, M Hashimoto J Antibiot (Tokyo). 1990 Apr;43(4):344-51. doi: 10.7164/antibiotics.43.344.
The structures of compounds 3 (and 4) and 5 (and 6) derived from the natural products WS1358A1 (1) (and B1 (2)) have been determined by their spectroscopic evidence. By taking advantage of these transformations, an improved synthesis of A1 (1, racemate) has been achieved.
3. Studies on new dehydropeptidase inhibitors. II. Structural elucidation and synthesis of WS1358A1 and B1
S Takase, I Uchida, S Hashimoto, H Tanaka, M Hashimoto J Antibiot (Tokyo). 1990 Jan;43(1):38-42. doi: 10.7164/antibiotics.43.38.
The structures of WS1358A1 and B1, new dehydropeptidase inhibitors isolated from Streptomyces parvulus subsp. tochigiensis No. 1358, have been established to be 2-hydroxy-2-hydroxyaminocarbonyl-3-methylglutaric acid (1) and 2-hydroxy-2-hydroxyaminocarbonylglutaric acid (2), respectively, on the basis of spectroscopic evidence and synthesis of the racemates.

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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