135582-87-5Relevant academic research and scientific papers
Structural Insights Lead to a Negamycin Analogue with Improved Antimicrobial Activity against Gram-Negative Pathogens
McKinney, David C.,Basarab, Gregory S.,Cocozaki, Alexis I.,Foulk, Melinda A.,Miller, Matthew D.,Ruvinsky, Anatoly M.,Scott, Clay W,Thakur, Kumar,Zhao, Liang,Buurman, Ed T.,Narayan, Sridhar
, p. 930 - 935 (2015)
Negamycin is a natural product with antibacterial activity against a broad range of Gram-negative pathogens. Recent revelation of its ribosomal binding site and mode of inhibition has reinvigorated efforts to identify improved analogues with clinical potential. Translation-inhibitory potency and antimicrobial activity upon modification of different moieties of negamycin were in line with its observed ribosomal binding conformation, reaffirming stringent structural requirements for activity. However, substitutions on the N6 amine were tolerated and led to N6-(3-aminopropyl)-negamycin (31f), an analogue showing 4-fold improvement in antibacterial activity against key bacterial pathogens. This represents the most potent negamycin derivative to date and may be a stepping stone toward clinical development of this novel antibacterial class.
Organocatalytic syn-aldol reactions of hydroxy ketones with (S)-isoserinal: Asymmetric synthesis of 6-deoxy-1,5-iminohexitols and related compounds
Nicolas, Cyril,Pluta, Roman,Pasternak-Suder, Monika,Martin, Olivier R.,Mlynarski, Jacek
, p. 1296 - 1305 (2013/04/10)
An improved and convenient preparation of protected (S)-isoserinal on a large scale is reported. This key intermediate was reacted through organocatalyzed aldol reaction or Wittig based chain extension and functionalization to give enantiopure 1,5,6-trideoxy-1,5-imino-hexitols such as 10a (L-manno) and 10b (D-gluco). These two compounds are of interest as glycosidase inhibitors. The elaborated organocatalytic process includes diastereoselective syn aldol reaction of (S)-isoserinal hydrate and hydroxyacetone or 1-hydroxy-2-octanone and is promoted by various amino acid-based catalysts. Diastereoselectivities of up to 8:1 were achieved, thus establishing a new, efficient synthetic route to these important carbohydrate mimics. A novel protocol for the preparation of 1,5,6-trideoxy-1,5-imino-L- mannitol and 1,5,6-trideoxy-1,5-imino-D-glucitol is reported. The key steps include organocatalyzed syn-selective direct aldol reaction of hydroxyacetone and CBz-protected isoserinal hydrate, followed by reductive amination/ cyclization. Copyright
Short synthesis of (+)-1-deoxynojirimycin via a diastereoselective reductive coupling of alkyne and -chiral aldehyde
Zhou, Bing,Tang, Huanyu,Feng, Huijin,Li, Yuanchao
supporting information; experimental part, p. 2709 - 2712 (2011/12/15)
A short, highly diastereoselective synthesis of (+)-1-deoxynojirimycin from readily available l-isoserine with overall yield of 32.0% in eight steps is described. The key step includes a diastereoselective syn-coupling reaction of Cbz-protected (S)-iso-serinal acetonide 6 and vinylzinc nucleophile, generated conveniently from a protected propargyl alcohol 7 by a hydrozirconation- transmetalation sequence. Significantly, not only does this simple flexible strategy provide a concise approach to (+)-1-deoxynojirimycin, but it also can readily be adopted for the synthesis of other stereoisomers of the 1-deoxynojirimycin family from l- or d-iso-serine through different coupling conditions and stereoselective -epoxidation of allylic alcohol 4 by the same procedures. Georg Thieme Verlag Stuttgart · New York.
A short, versatile chemical synthesis of L- And D-amino acids stereoselectively labelled solely in the beta position
Lowpetch, Kreingkrai,Young, Douglas W.
, p. 3348 - 3356 (2007/10/03)
L- and D-Amino acids which are stereoselectively labelled solely either in the 3-pro-R or in the 3-pro-S-positions have been prepared by a relatively short chemical synthesis in ee of 81 to 86%. This involves Sharpless' aminohydroxylation and cyclisation
Erhoehung der Effizienz der katalytischen asymmetrischen Aminohydroxylierung durch N-Halogencarbamat-Salze
Li, Guigen,Angert, Hubert H.,Sharpless, K. Barry
, p. 2995 - 2999 (2007/10/03)
Keywords: Aminoalkohole; Asymmetrische Aminohydroxylierung; Carbamate; Katalyse
Total synthesis of the biphenomycins; II. Synthesis of protected (2S,4R)-4-hydroxyornithines
Schmidt,Meyer,Leitenberger,Stabler,Lieberknecht
, p. 409 - 413 (2007/10/02)
Improved synthetic methods for the preparation of three differently protected (2S,4R)-4-hydroxyornithine (10, 16, 24) have been developed which obviously can be used for the construction of the other stereoisomers. Formation of the corresponding α,β-dideh
