76215-89-9Relevant academic research and scientific papers
IMINOHEPTITOLS AS GLYCOSIDASE INHIBITORS: SYNTHESIS OF, AND MANNOSIDASE AND FUCOSIDASE INHIBITION BY, Α-HOMOMANNOJIRIMYCIN AND 6-EPI-HOMOMANNOJIRIMYCIN
Bruce, Ian,Fleet, George W. J.,Bello, Isabelle Cenci di,Winchester, Bryan
, p. 7257 - 7260 (1989)
C-2 and C-6 of a heptonolactone are joined together by nitrogen to afford α-homomannojirimycin (HMJ) and 6-epi-α-homomannojirimycin; the inhibition of some α-mannosidases and α-fucosidases by these iminoheptitols is reported.
Towards new antibiotics targeting bacterial transglycosylase: Synthesis of a Lipid II analog as stable transition-state mimic inhibitor
Wang, Xiaolei,Krasnova, Larissa,Wu, Kevin Binchia,Wu, Wei-Shen,Cheng, Ting-Jen,Wong, Chi-Huey
supporting information, p. 2708 - 2712 (2018/04/06)
Described here is the asymmetric synthesis of iminosugar 2b, a Lipid II analog, designed to mimic the transition state of transglycosylation catalyzed by the bacterial transglycosylase. The high density of functional groups, together with a rich stereochemistry, represents an extraordinary challenge for chemical synthesis. The key 2,6-anti- stereochemistry of the iminosugar ring was established through an iridium-catalyzed asymmetric allylic amination. The developed synthetic route is suitable for the synthesis of focused libraries to enable the structure–activity relationship study and late-stage modification of iminosugar scaffold with variable lipid, peptide and sugar substituents. Compound 2b showed 70% inhibition of transglycosylase from Acinetobacter baumannii, providing a basis for further improvement.
Eight stereoisomers of homonojirimycin from d -mannose
Lenagh-Snow, Gabriel M. J.,Jenkinson, Sarah F.,Newberry, Scott J.,Kato, Atsushi,Nakagawa, Shinpei,Adachi, Isao,Wormald, Mark R.,Yoshihara, Akihide,Morimoto, Kenji,Akimitsu, Kazuya,Izumori, Ken,Fleet, George W.J.
supporting information; experimental part, p. 2050 - 2053 (2012/06/18)
Although there are 32 6-azidoheptitols, there are only 16 homonojirimycin (HNJ) stereoisomers. Two epimeric azidoalditols derived from d-mannose allow the synthesis in water of eight stereoisomers of HNJ.
Intermediates for incorporation of tetrahydroxypipecolic acid analogues of α- and β-D-mannopyranose into combinatorial libraries: Unexpected nanomolar-range hexosaminidase inhibitors. Synthesis of α- and β- homomannojirimycin
Shilvock, John P.,Nash, Robert J.,Lloyd, Janet D.,Winters, Ana L.,Asano, Naoki,Fleet, George W. J.
, p. 3505 - 3516 (2007/10/03)
Homoazasugars have the distinction as a class of natural products in that most of them have been synthesised before they were isolated. Syntheses of α-1 and β-homomannojirimycin 2 rely on the stereoselective and chemoselective sodium cyanoborohydride reduction of a [2.2.2] bicyclic imino lactone (6) to give a single [2.2.2] bicyclic amino-lactone (7). Methanolysis of 7 under basic conditions is accompanied by efficient epimerisation of the first formed α-amino-ester (8) to the more stable β-amino-ester (9) in which the 2,6-substitutents are equatorial. Both 7 and 9 are suitable intermediates for the incorporation of tetrahydroxypipecolic acid derivatives into combinatorial libraries containing α- and β-C-glycosyl analogues of aza-D-mannopyranose, respectively. Methylamides derived from 7 and 9 are shown to be specific and potent inhibitors of two β-N-acetylglucosaminidases but have no effect on an α-N-acetylgalactosaminidase. The synthesis of α- 14 and β-17 manno-pipecolic acids is also reported.
Synthesis of &β-1-Homonojirimycin and &β-1-Homomannojirimycin using the Enzyme Aldolase
Holt, Karen E.,Leeper, Finian J.,Handa, Sheetal
, p. 231 - 234 (2007/10/02)
The four stereoisomers of the four-carbon azido sugar 11 have been stereoselectively synthesised by a route involving Sharpless epoxidation and all are found to be substrates for rabbit muscle fructose 1,6-bisphosphate aldolase, giving (after treatment wi
Iminoheptitols as glycosidase inhibitors: Synthesis of α-homomannojirimycin, 6-epi-α-homomannojirimycin and of a highly substituted pipecolic acid
Bruce,Fleet,Di Belo,Winchester
, p. 10191 - 10200 (2007/10/02)
In a search for a mannopyranose analogue which inhibits α-mannosidases but not α-fucosidases, α-homonojirimycin was prepared; the syntheses of 6-epi-α-homonojirimycin and of 2,6-dideoxy-2,6-imino-L-glycero-D-talo-heptonic acid (a highly substituted pipecolic acid) are also reported.
