Beta-lactone

Chemical Designations - Synonyms Betaprone Hydracrylic acid, beta-lactone 2-Oxetanone Propanolide beta-Propionolactone Chemical Formula OCH2CH2CO. 

Hydracrylic Acid, Beta-Lactone Beta-Prop Iolactone... 

Bottcher T, Sieber SA (2008) Beta-lactones as privileged structures for the active-site labeling of versatile bacterial enzyme classes. Angew Chem Int Ed Engl 47 4600... 

Phenylglyoxylate esters undergo type II elimination in a unique fashion in that the alcohol portion is oxidized to a ketone or aldehyde while the benzoylcarboxy portion forms a hydroxyketene [18]. The intermediate 1,4-biradicals do not cyclize, presumably because of the strain in a beta-lactone. 

Craiu, a., Gaczynska, M., Akopian, T, Gramm, C. F., Fenteany, G., Goldberg, A.L., Rock, K. L., Lactacystm and dasto-lactacystin beta-lactone modify multiple proteasome beta-subunits and inhibit intracellular protein degradation and major histocompatibility complex class 1 antigen presentation. J. Biol. Chem. 1997,... 

Groll M, Huber R, Potts BC. Crystal structures of Salinospo-ramide A NPI-0052 and B NPI-0047 in complex with the 20S proteasome reveal important consequences of beta-lactone ring opening and a mechanism for irreversible binding. J. Am. Chem. Soc. 2006 128 5136-5141. 

SYNONYMS Betaprone, BPL, 3-hydroxy-propionic acid, beta-lactone, 3-propiolactone. 

CAS-No [57-57-8] hydracryllc acid beta-lactone 2-oxetanona propanollda 1,3-proplolactone... 

Bottcher, T. and Sieber, S.A. (2008) Beta-lactones as specific inhibitors of ClpP attenuate the production of extracellular virulence factors of Staphylococcus aureus. /. Am. Chem. Soc., 130 (44), 14400-14401. 

Adamus et al. [26] studied copolymers with units of beta-butyrolactone (HB) and2-hydroxyhexanoic acid (2HHA) with ESI. The mixture of HB and 2HHA was stirred and heated at 70°C. The heating was continued until the racemic beta-butyrolactone was consumed, as determined by infrared (IR) spectroscopy (disappearance of beta-lactone carbonyl absorption band at 1815/cm).The copolymer yield was higher than 80%. The subsequent SEC analysis allowed to estabhsh that the polydispersity index is reasonably large ( I =1.6). 

R-3-hydroxybutyrate (3HB) was reported to be used for the synthesis of carbapenem antibiotics [6]. Other 3-hydroxy acids were also reported to be used as chiral building blocks for the synthesis of macrolides such as pyrenophorin, col-letodiol, grahamimycin A1 and elaiophylidene [6]. The transformation of 3-hydroxyaIkanoates (3HA) to their dioxanone enolates allows the subsequent synthesis of various 3HA derivatives. 3HB dioxanone enolates can be used as intermediates for synthesis of beta-lactones and 2-aIkylated 3HB [6]. 

RETA.PROPIO. LACTONE C,H,0, HydroacryUc Mid, beta-lactone 3-Hydroxy-propionic acid beta-Lactone 2-Oxetanone Betaprone Propanolide Propiolactone Propionic acid 3 Hydroxy-beta-lactone beta Propiolactone beta-Proprolactonc BPL Acetates, halogeiu, thiocyanates, and thiosulphates 15ft 2.9 ... 

Soucy F, Grenier L, Behnke ML, Destree AT, McCormack TA, Adams J, Plamondon L. A novel and efficient synthesis of a highly active analogue of clasto-lactacystin beta-lactone. J. Am. Chem. Soc. 1999 121 9967 9976. 

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