Biosynthesis and Biological Activity of Carbasugars

Abstract

The first synthesis of carbasugars, compounds in which the ring oxygen of a monosaccharide had been replaced by a methylene moiety, was described in 1966 by Professor G. E. McCasland's group. Seven years later, the first true natural carbasugar (5a-carba-R-D-galactopyranose) was isolated from a fermentation broth of Streptomyces sp. MA-4145. In the following decades, the chemistry and biology of carbasugars have been extensively studied. Most of these compounds show interesting biological properties, especially enzymatic inhibitory activities, and, in consequence, an important number of analogues have also been prepared in the search for improved biological activities. The aim of this review is to give coverage on the progress made in two important aspects of these compounds: the elucidation of their biosynthesis and the consideration of their biological properties, including the extensively studied carbapyranoses as well as the much less studied carbafuranoses.

Synthesis of 4a‐Carba‐d‐lyxofuranose Derivatives and Their Evaluation as Inhibitors of GH38 α‐Mannosidases

“…Then, charcoal (0.5 g) was added to a stirred solution of cyclopentene 13 in a mixture of EtOAc/hexanes (1:1, v/v, 70 mL), and the mixture was stirred for 30 min. 1 (3aR,4R,6R,6aS) M.p.…”

“…The resulting mixture was filtered, and a filter cake was washed with MeOH (5 mL), and the filtrate was concentrated under reduced pressure. 1 and DMAP (26 mg, 0.21 mmol) in CH 2 Cl 2 (6.5 mL) at 0°C, and the mixture was stirred at room temperature overnight. [27] [α] D 20 = -12.9 (c 1.0, MeOH), ref.…”

“…[1] These cyclitols can be considered as furanose or pyranose analogues in which the endocyclic oxygen is replaced by a methylene group. [1] These cyclitols can be considered as furanose or pyranose analogues in which the endocyclic oxygen is replaced by a methylene group.…”

Synthesis of Oxaphosphinane‐Based Pseudodisaccharides

“…It is now well established that carbohydrates play critical and central roles in key recognition [a] Institut Charles Gerhardt -UMR 5253, CNRS 5253, AM2N, ENSCM, events. [4,5] In this context, the 6′-thiodisaccharide 1 was found to inhibit -(1→4)-galactosyltransferase with an inhibition constant (K i ) in the millimolar range. These properties are manifested by potent effects related to inflammation, cancer, and infection.…”

“…, CH-4′), 79.9 (s, 1 C, CH-3′), 81.6 (d, 2 J C,P = 5 5. Hz, 1 C, CH-2), 84.9 (s, 1 C, CH-2′), 106.4 (d,3 J C,P = 7.1 Hz, 1 C, CH-1′), 112.7 [s, 1 C, Cq(CH 3 ) 2 ], 126.4 (d, 1 J C,P = 142.0 Hz, 1 C, Cq ar ), 127.5, 127.7, 127.8, 127.88, 127.9, 127.9, 128.3 (d, 3 J C,P = 13.4 Hz, 1 C, CH m ), 128.4, 128.4, 128.5, 133.3 (d, 2 J C,P = 9.9 Hz, 1 C, CH o ), 133.5 (d, 4 J C,P = 2.6 Hz, 1 C, CH p ), 137.5 (s, 1 C, CqBn), 138.0 (s, 1 C, CqBn), 138.2 (s, 1 C, CqBn) ppm.…”