Gabosine A

Gabosine A

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Category Enzyme inhibitors
Catalog number BBF-01472
CAS 127545-53-3
Molecular Weight 158.15
Molecular Formula C7H10O4
Purity >98%

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Description

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

Specification

Synonyms (-)-gabosine A; (4R,5R,6S)-4,5,6-trihydroxy-2-methyl-2-cyclohexen-1-one
IUPAC Name (4R,5R,6S)-4,5,6-trihydroxy-2-methylcyclohex-2-en-1-one
Canonical SMILES CC1=CC(C(C(C1=O)O)O)O
InChI InChI=1S/C7H10O4/c1-3-2-4(8)6(10)7(11)5(3)9/h2,4,6-8,10-11H,1H3/t4-,6-,7-/m1/s1
InChI Key YNPFEYUTCGDFDD-QPPQHZFASA-N

Properties

Boiling Point 330.1±42.0 °C at 760 mmHg
Melting Point 182°C
Density 1.5±0.1 g/cm3

Reference Reading

1. Carbasugar Synthesis via Vinylogous Ketal: Total Syntheses of (+)-MK7607, (-)-MK7607, (-)-Gabosine A, (-)-Epoxydine B, (-)-Epoxydine C, epi-(+)-Gabosine E and epi-(+)-MK7607
Soumik Mondal, Kana M Sureshan J Org Chem. 2016 Dec 2;81(23):11635-11645. doi: 10.1021/acs.joc.6b01876. Epub 2016 Nov 10.
Carbasugars, the carbocyclic analogues of sugars, constitute an important class of natural products with more than 140 members known and have attracted much attention due to their diverse biological activities like anticancer, antibacterial, herbicidal, and various enzyme inhibitory activities. As many carbohydrates are involved in various cellular signaling pathways, there is great interest in synthesis and biological exploration of carbasugars. Herein, we have developed a methodology to install an α,β-unsaturated aldehyde functionality on different inositols and derivatives by vinylogous elimination of the O-protecting group under mildly acidic condition. We have illustrated the versatility and utility of our methodology by the total syntheses of seven carbasugars viz. (-)-MK7607, (-)-gabosine A, (-)-epoxydine B, (-)-epoxydine C, (+)-MK7607, 1-epi-(+)-MK7607 and 1-epi-(+)-gabosine E.
2. A divergent strategy to synthesize gabosines featuring a switchable two-way aldol cyclization
Xing Yang, Po Yuan, Feng Shui, Yuqin Zhou, Xiaochuan Chen Org Biomol Chem. 2019 Apr 17;17(16):4061-4072. doi: 10.1039/c9ob00469f.
Gabosines and their natural analogues, belonging to C7 carbasugars, have attracted great attention in synthesis due to their rich structural variety and promising biological activities. A new diversity-oriented approach for the gabosine-type carbasugars based on a tunable regioselective aldol cyclization of flexible precursor 2 is explored. Two cyclization modes (A and B) of the precursor can be well controlled by switching promoters to selectively produce two resulting cyclohexa(e)nones 3 and 10, both of which are versatile intermediates for various C7 carbasugars. After the conversion of 3 to eight natural carbasugars, the utility of intermediate 10 is illustrated by the first synthesis of (-)-gabosine L, as well as the new synthesis of (-)-gabosine A, (-)-gabosine B, (-)-gabosine N and (-)-gabosine O. The chemical structure and the absolute configuration of (-)-gabosine L are confirmed by its total synthesis.
3. Facile syntheses of (+)-gabosines A, D, and E
Tony K M Shing, Hau M Cheng Org Biomol Chem. 2009 Dec 21;7(24):5098-102. doi: 10.1039/b911810a. Epub 2009 Oct 16.
(+)-Gabosines A (12), D (4), and E (5), which share the same trihydroxycyclohexenone skeleton, were synthesized from enone 11 as the common intermediate. The key building block 11 was accessed by an intramolecular aldol cyclization of a diketone derived from D-glucose (8).

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