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Gabosine C

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Category Enzyme inhibitors
Catalog number BBF-01473
CAS
Molecular Weight 174.15
Molecular Formula C7H10O5
Purity >98%

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Capabilities & Facilities

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

A polar ring alcohol produced by the strain of Streptomycetes. Gabosine C has the ability of inhibiting Glyoxylase I.

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Synonyms (+)-Gabosine C; (4R,5R,6R)-4,5,6-Trihydroxy-2-(hydroxymethyl)-2-cyclohexen-1-one
IUPAC Name (4S,5S,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)cyclohex-2-en-1-one
Canonical SMILES C1=C(C(=O)C(C(C1O)O)O)CO
InChI InChI=1S/C7H10O5/c8-2-3-1-4(9)6(11)7(12)5(3)10/h1,4,6-9,11-12H,2H2/t4-,6-,7+/m0/s1
InChI Key DEJZWTDEKQRWLD-JSKYLQRQSA-N
Boiling Point 429.4±45.0 °C at 760 mmHg
Melting Point 113-114°C
Density 1.7±0.1 g/cm3
1. How a diversity-oriented approach has inspired a new hypothesis for the gabosine biosynthetic pathway. A new synthesis of (+)-gabosine C
Miguel Ángel Fresneda, Ramon Alibés, Josep Font, Pau Bayón, Marta Figueredo Org Biomol Chem. 2013 Oct 14;11(38):6562-8. doi: 10.1039/c3ob41183d. Epub 2013 Aug 28.
A new synthesis of (+)-gabosine C has been accomplished as part of a general diversity-oriented approach that also delivered the previously unknown (-)-4-epi-gabosine C. The identification of the unexpected intermediate (+)-8, together with the isolation of ketones 9 and 10 in previous investigations, prompted us to formulate a new hypothesis for the biosynthesis of gabosines, based on a keto-enol equilibrium cascade pathway starting from 2-epi-5-epi-valiolone, along which the necessary precursors for all the different types of gabosines are generated.
2. Toward synthesis of carbasugars (+)-gabosine C, (+)-COTC, (+)-pericosine B, and (+)-pericosine C
D Chanti Babu, Ch Bhujanga Rao, K Venkatesham, J Jon Paul Selvam, Y Venkateswarlu Carbohydr Res. 2014 Mar 31;388:130-7. doi: 10.1016/j.carres.2013.08.008. Epub 2013 Aug 20.
Asymmetric total synthesis of (+)-gabosine C, (+)-pericosine B, and (+)-pericosine C has been reported from readily available d-(-)-isoascorbic acid and d-ribose involving Grubbs ring closing metathesis, Morita-Baylis-Hillman (MBH) reaction, and Luche reduction.

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