38129-37-2

Usage

Uses

Used in Pharmaceutical Industry:
Bicozamycin is used as an antibiotic for targeting and treating bacterial infections, particularly those caused by Gram-negative bacteria. Its unique mode of action, which involves the inhibition of the Rho protein in E. coli, makes it a potentially effective agent in combating antibiotic-resistant strains.
Used in Research and Development:
In the field of microbiology and pharmaceutical research, Bicozamycin serves as a valuable tool for studying the mechanisms of bacterial transcription and the role of the Rho protein in bacterial growth and replication. This can lead to the development of new antibiotics and a better understanding of bacterial resistance.
Used in Drug Resistance Studies:
Bicozamycin's selective activity against Gram-negative bacteria makes it an important compound in the study of drug resistance. It can be used to investigate the development of resistance in these bacteria and to develop strategies to overcome resistance, ultimately contributing to the development of more effective antibiotics.

Upstream product

• 63777-16-2 dihydrobicyclomycin 2',3'-acetonide 
• 95237-56-2 (1S,6R)-6-<(tert-butyldimethylsilyl)oxy>-1-<(1S,2S)-2-methyl-1,2,3-trihydroxypropyl>-5-methylene-7,9-diaza-2-oxabicyclo<4.2.2>decane-8,10-dione 
• 95694-73-8 (+)-N,N'-bis(p-methoxybenzyl)-1'-O-(trifluoroacetyl)-2',3'-O-isopropylidene-bicyclomycin 
• 61-90-5 L-leucine 
• 73-32-5 L-isoleucine 
• 92098-15-2 8,10-bis(p-methoxybenzyl)-8,10-diaza-5-methylene-2-oxabicyclo<4.2.2>decane-7,9-dione 
• 95694-70-5 (1S,6R)-6-hydroxy-1-<(1S,2S)-2,3-O-isopropylidene-2-methyl-1,2,3-trihydroxypropyl>-7,9-bis(p-methoxybenzyl)-5-methylene-7,9-diaza-2-oxabicyclo<4.2.2>decane-8,10-dione 
• 92098-16-3 8,10-bis(p-methoxybenzyl)-8,10-diaza-5-methylene-6-hydroxy-2-oxabicyclo<4.2.2>decane-7,9-dione 
• 92098-12-9 8,10-bis(p-methoxybenzyl)-8,10-diaza-5-(hydroxymethyl)-2-oxabicyclo<4.2.2>decane-7,9-dione 
• 95782-41-5 8,10-bis(p-methoxybenzyl)-8,10-diaza-5-<(methylsulfonyl)methyl>-2-oxabicyclo<4.2.2>decane-7,9-dione 
• 95237-57-3 (1S,6R)-6-<(tert-butyldimethylsilyl)oxy>-1-<(1S,2S)-2,3-O-isopropylidene-2-methyl-1,2,3-trihydroxypropyl>-5-methylene-7,9-diaza-2-oxabicyclo<4.2.2>decane-8,10-dione 
• 95237-55-1 (1S,6R)-6-<(tert-butyldimethylsilyl)oxy>-1-<(1S,2S)-2,3-O-isopropylidene-2-methyl-1,2,3-trihydroxypropyl>-7,9-bis(p-methoxybenzyl)-5-methylene-7,9-diaza-2-oxabicyclo<4.2.2>decane-8,10-dione 
• 63777-16-2 bicyclomycin acetonide 
• 92125-62-7 N,N'-bis(p-methoxybenzyl)-1'-O-(trifluoroacetyl)-2',3'-O-isopropylidene-bicyclomycin 

Downstream Products

• 121231-86-5 (R)-2-Acetylamino-3-((1S,2S,3S,6S,7R)-2,3,6-trihydroxy-3-methyl-12,13-dioxo-5,10-dioxa-11-aza-tricyclo[5.3.3.0^1,6]tridec-7-ylmethylsulfanyl)-propionic acid methyl ester 
• 120546-81-8 2-({3-[4-(2-Benzoylamino-2-methylcarbamoyl-ethyl)-imidazol-1-ylmethyl]-2-hydroxy-tetrahydro-furan-2-carbonyl}-amino)-3,4-dihydroxy-4-methyl-tetrahydro-furan-2-carboxylic acid amide 
• 71994-04-2 (1S)-6-hydroxy-9-(1-hydroxy-1-methyl-ethyl)-5-methylene-8,10-dioxo-2-oxa-7,9-diaza-bicyclo[4.2.2]decane-1-carbaldehyde 1,9-cyclohemiacetal 
• 71993-92-5 (1S)-6-benzoyloxy-1-((1S,2S)-1-benzoyloxy-2-hydroxy-2-methyl-3-(Ξ)-tetrahydropyran-2-yloxy-propyl)-5-methylene-2-oxa-7,9-diaza-bicyclo[4.2.2]decane-8,10-dione 
• 71993-91-4 (1S)-1-((1S,2S)-1-benzoyloxy-2-hydroxy-2-methyl-3-(Ξ)-tetrahydropyran-2-yloxy-propyl)-6-hydroxy-5-methylene-2-oxa-7,9-diaza-bicyclo[4.2.2]decane-8,10-dione 
• 71994-02-0 (2Ξ,4S)-4-hydroxy-4-((1S)-6-hydroxy-5-methylene-8,10-dioxo-2-oxa-7,9-diaza-bicyclo[4.2.2]dec-1-yl)-3-methyl-but-2-enoic acid 4-nitro-benzyl ester 
• 66305-90-6 (1S)-6-hydroxy-1-((1S,2S)-1,2,3-trihydroxy-2-methyl-propyl)-2-oxa-7,9-diaza-bicyclo[4.2.2]decane-5,8,10-trione 5-phenylhydrazone 
• 71993-93-6 (1S)-1-((1S,2S)-1-benzoyloxy-2,3-dihydroxy-2-methyl-propyl)-6-hydroxy-5-methylene-2-oxa-7,9-diaza-bicyclo[4.2.2]decane-8,10-dione 
• 66310-61-0 (1S)-6-hydroxy-5-(2-oxo-2-phenyl-ethylidene)-1-((1S,2S)-1,2,3-trihydroxy-2-methyl-propyl)-2-oxa-7,9-diaza-bicyclo[4.2.2]decane-8,10-dione 
• 66460-05-7 (1S)-6-hydroxy-5-((Z)-2-oxo-propylidene)-1-((1S,2S)-1,2,3-trihydroxy-2-methyl-propyl)-2-oxa-7,9-diaza-bicyclo[4.2.2]decane-8,10-dione (Ξ)-5,6-cyclohemiacetal 
• 143037-41-6 (1S,2S,3S,7R,8S)-2,3,7-Trihydroxy-3-methyl-8-phenylsulfanylmethyl-11-oxa-5,13-diaza-tricyclo[5.4.2.0^1,5]tridecane-6,12-dione 
• 575443-95-7 5a-(4-tert-butylphenylsulfanyl)dihydrobicyclomycin 2',3'-acetonide 
• 575443-94-6 5a-(2-aminophenylsulfanyl)dihydrobicyclomycin 2',3'-acetonide 

Relevant academic research and scientific papers

The biosynthesis of the Streptomyces antibiotic bicyclomycin

Bicyclomycin 5 is biosynthesized in Streptomyces sapporonensis from L-leucine 2 and L-isoleucine 1 by way of the naturally occurring diketopiperazine 3 and dihydrobicyclomycin 4. The mode of incorporation of (2S,4R)-[5,5,5-2H3]leucine into 5 (and 4) shows that the entry of hydroxy group at C-2' occurs with unusual inversion of configuration. The results of inhibition studies permit a useful working hypothesis to be advanced for bicyclomycin biosynthesis.

Chiral Synthesis of Bicyclomycin and Diastereomeric Stereoselectivity of the Key Aldol Condensation

Optically pure bicyclomycin (1) was synthesized via aldol condensation of racemic 7,9-bis(p-methoxybenzyl)-5-methylene-6--7,9-diaza-2-oxabicyclodecane-8,10-dione (2) with 2,3-di-O-isopropylidene-2-C-methyl-L-glyceraldehyde (3).The major condensation product 4 was then N-de(p-methoxybenzyl)ated and O-deisopropylidenated simultaneously with CAN and O-de(tert-butyldimethylsilyl)ated with Bu4NF under finely optimized conditions, respectively, to give 1.The structures of three other diastereomers of 4 were elucidated through comparisonwith the products of the aldol condensation of optically pure 2 and 3.The compounds (+)-2 and (-)-2 were prepared by diastereomeric separation of the synthetic precursor of 2, i.e., 5,6-dihydroxy-7,9-bis(p-methoxybenzyl)-7,9-diaza-2-oxabicyclodecane-8,10-dione as its (-)-MTPA ester, followed by the previously established four-step conversion.The stereoselectivity of the aldol condensation was explained by the chair conformation-like transition states.

THE CHIRAL SYNTHESIS OF BICYCLOMYCIN

The optically active bicyclomycin was succesfully synthesized in 17 steps from N,N'-diacetyl-anhydroglycine.

TOTAL SYNTHESIS OF BICYCLOMYCIN

Total synthesis of (+/-)-bicyclomycin was achieved in 19 steps starting from diketopyperazine.