97551-67-2Relevant academic research and scientific papers
Synthesis of new 3- and 4-substituted analogues of acyl homoserine lactone quorum sensing autoinducers
Olsen,Severinsen,Rasmussen,Hentzer,Givskov,Nielsen
, p. 325 - 328 (2007/10/03)
The quorum sensing mechanism in Gram-negative bacteria uses small intercellular signal molecules, N-acyl-homoserine lactones (AHLs), to control transcription of specific genes in relation to population density. In this communication, we describe the parallel synthesis of new AHL analogues, in which substituents have been introduced into the 3- and 4-positions of the lactone ring. These analogues have been screened for their ability to activate and inhibit a Vibrio fischeri LuxI/LuxR-derived quorum sensing reporter system.
Chelation controlled 1,3-dipolar cycloaddition of 5,6-dihydro-5-phenyl- 1,4-oxazin-2-one N-oxide with allyl alcohols: A short-step synthesis of clavalanine intermediate
Tamura, Osamu,Kuroki, Takahiro,Sakai, Yuta,Takizawa, Jun-ichi,Yoshino, Jun,Morita, Yasuhiro,Mita, Naka,Gotanda, Kentoku,Sakamoto, Masanori
, p. 895 - 898 (2007/10/03)
(R)-5,6-Dihydro-5-phenyl-1,4-oxazin-2-one N-oxide {(R)-2 } reacts with allyl alcohols 3a-c in the presence of magnesium bromide from the less hindered face via exo-mode to afford corresponding cycloadducts 4a-c with excellent stereoselection. Treatment of (R)-2 with three equivalents of racemic secondary allyl alcohols 3d-g under the same conditions causes partial kinetic resolution to give 4d-g as main products among eight possible stereoisomers. Cycloadduct ent-4a from (S)-2 and 3a was converted directly to g-lactone 6, which is known as the key synthetic intermediate of antibiotic clavalanine.
A facile transformation of the δ-hydroxy-α-amino lactones from α- furfuryl amide
Liao, Li-Xin,Zhou, Wei-Shan
, p. 12571 - 12584 (2007/10/03)
(S)- and (R)- α- furfuryl amides, obtained from the kinetic resolution of (R, S)- α- furfuryl amide using the modified Sharpless asymmetric epoxidation, have been transformed into four 8-hydroxy α- amino lactones (1S, 3S)-1, (1R, 3R)-1, (1S, 3R)-1, (1R, 3S)-1, using sharpless asymmetric dihydroxylation as the key step. The much more efficient method of the addition of chiral aldimine 10 with allylic Grignard reagent for preparation of (S, S)-1 was also achieved.
Rapid syntheses of 3-amino-5-hydroxymethyl-γ-lactones from L- allylglycine
Girard, Anne,Greck, Christine,Genet, Jean Pierre
, p. 4259 - 4260 (2007/10/03)
(3R, 5R) and (3R, 5S) N-protected 3-amino-5-hydroxymethyl-γ-lactones were obtained by one dihydroxylation step from methyl N-protected L- allylglycinate.
A new approach to clavalanine β-lactam antibiotic: Transformation of chiral α-furfuryl amide into the δ-hydroxyl-α-amino lactones via asymmetrical dihydroxylation
Liao, Li-Xin,Zhou, Wei-Shan
, p. 6371 - 6374 (2007/10/03)
Transformation of chiral α-furfuryl amide obtained from kinetic resolution into four δ-hydroxyl-α-amino lactones by utilizing the Sharpless ADH reaction as a key step was achieved.
An efficient and concise entry to (-)-4,5-dihydroxy-d-threo-l norvaline. Formal synthesis of clavalanine
Ariza, Jesus,Font, Josep,Ortuno, Rosa M.
, p. 1979 - 1982 (2007/10/02)
The title amino acid (2) has been synthesized for the first time in a seven-step sequence from D-ribonolactone, in 20% overall yield. Since the N-carbamoyl derivative of (2) in its y-lactone form has been used to prepare clavalanine, a formal total synthe
Amino acids and peptides; 75. Synthesis of di- and trihydroxyamino acids - Construction of lipophilic tripalmitoyldihydroxy-α-amino acids
Schmidt,Lieberknecht,Kazmaier,Griesser,Jung,Metzger
, p. 49 - 55 (2007/10/02)
Suitable protected derivatives of trihydroxynorleucines-[(2S,4S,5S)- and (2R,4S,5S)-2-amino-4,5,6-trihydroxyhexanoic acid], of all isomeric dihydroxynorvalines [2-amino-4,5-dihydroxypentanoic acids), of all isomeric 2-amino-6,7-dihydroxyheptanoic acids an
Practical Asymmetric Syntheses of α-Amino Acids through Carbon-Carbon Bond Constructions on Electrophilic Glycine Templates
Williams, Robert M.,Sinclair, Peter J.,Zhai, Dongguan,Chen, Daimo
, p. 1547 - 1557 (2007/10/02)
The optically active D- and L-erythro-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-ones (3) and D- and L-erythro-4-(tert-butoxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-ones (3) can be efficiently brominated to serve as electrophilic glycine templates for the asymmetric synthesis of amino acids.It was found that coupling to these templates can proceed with either net retention or net inversion of stereochemistry.The final deblocking to the amino acids is accomplished with either dissolving-metal reduction or catalytic hydrogenolysis.The syntheses of β-ethyl aspartic acid, norvaline, allylglycine, alanine, norleucine, homophenylalanine, p-methoxyhomophenylalanine, cyclopentylglycine, and cyclopentenylglycine and a formal synthesis of clavalanine are described.In addition, the direct asymmetric syntheses of N-t-BOC-allylglycine and N-t-BOC-cyclopentenylglycine are described.
Clavalanine (Ro 22-5417), a New Clavam Antibiotic from Streptomyces clavuligerus. 4. A Stereorational Synthesis
Bernardo, Silvano De,Tengi, John P.,Sasso, Gino J.,Weigele, Manfred
, p. 3457 - 3462 (2007/10/02)
Clavalanine (Ro 22-5417), a new β-lactam antibiotic, 3-hept-3-yl>-L-alanine (1), was synthesized by a route in which D-xylose (4) supplied the stereochemical requirements.From 4 was elaborated a (2S,4S)-2-amino-4,5-
