119557-99-2Relevant articles and documents
An approach to 8 stereoisomers of homonojirimycin from d-glucose via kinetic & thermodynamic azido-γ-lactones
Glawar, Andreas F. G.,Jenkinson, Sarah F.,Newberry, Scott J.,Thompson, Amber L.,Nakagawa, Shinpei,Yoshihara, Akihide,Akimitsu, Kazuya,Izumori, Ken,Butters, Terry D.,Kato, Atsushi,Fleet, George W. J.
, p. 6886 - 6899 (2013)
Crystal structures were obtained for the two C2 epimeric azido-γ-lactones 2-azido-2-deoxy-3,5:6,7-di-O-isopropylidene-d-glycero-d- ido-heptono-1,4-lactone and 2-azido-2-deoxy-3,5:6,7-di-O-isopropylidene-d- glycero-d-gulo-heptono-1,4-lactone prepared from kinetic and thermodynamic azide displacements of a triflate derived from d-glucoheptonolactone. Azido-γ-lactones are very useful intermediates in the synthesis of iminosugars and polyhydroxylated amino acids. In this study two epimeric azido-heptitols allow biotechnological transformations via Izumoring techniques to 8 of the 16 possible homonojirimycin analogues, 5 of which were isolated pure because of the lack of stereoselectivity of the final reductive amination. A side-by-side glycosidase inhibition profile of 11 of the possible 16 HNJ stereoisomers derived from d-glucose and d-mannose is presented.
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 (1992)
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.
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.
, p. 2050 - 2053 (2012)
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.
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.
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
Total Synthesis of (+)-α-Homonojirimycin
Aoyagi, Sakae,Fujimaki, Satoshi,Kibayashi, Chihiro
, p. 1457 - 1459 (2007/10/02)
The total synthesis of (+)-α-homonojirimycin, the first example of a naturally occurring azaheptose, was achieved in 13 steps utilizing the allylic alcohol 3 as a non-carbohydrate chiral building block.
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 (2007/10/02)
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.
A Facile, Practical Synthesis of 2,6-Dideoxy-2,6-imino-7-O-β-D-glucopyranosyl-D-glycero-L-gulo-heptitol (MDL 25,637)
Anzeveno, Peter B.,Creemer, Laura J.,Daniel, John K.,King, Chi-Hsin R.,Liu, Paul S.
, p. 2539 - 2542 (2007/10/02)
A facile synthetic route useful for large-scale preparation of the α-glucosidase inhibitor, 2,6-dideoxy-2,6-imino-7-O-β-D-glucopyranosyl-D-glycero-L-gulo-heptitol (1), is described.The protected heptononitrile 5, prepared in three steps from the readily available bisulfite adduct of nojirimycin (2), was stereospecifically converted to carboxylic acid 6 by acid hydrolysis (90percent TFA/Hg(TFA)2) and oxidation (N2O4).After reduction, the resultant amino alcohol 7 was N-protected and condensed with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl trichloroacetimidate to provide glucoside 9.Stepwise deprotection of 9 with transfer hydrogenation and base-catalyzed hydrolysis gave compound 1 in 26percent overall yield from 2.
