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1 dihydro-6-pentyl-2H-pyran-2-one (C10 massoia lactone).
2 between the C-9 amine and the Fukuyama-type lactone.
3 argets are functionally impaired by the beta-lactone.
4 with CO to give an O-[Zr] bonded borata-beta-lactone.
5 ylation of the diastereomeric tricyclic beta-lactone.
6 ished by their high content of a hydrophobic lactone.
7 lization reaction, leading to a triterpenoid lactone.
8 lysates with a model probe of threonine beta-lactone.
9 ovides an additional stereocenter within the lactone.
10 t was subsequently gelled with glucono delta-lactone.
11 the corresponding unreported unsaturated 1,7-lactones.
12 pective enantiopure, fused six-five bicyclic lactones.
13 opening reactions and reduction to saturated lactones.
14 um's acid derivatives and alkynes into delta-lactones.
15 transcriptional networks between PMA and DAG-lactones.
16 ted epoxides to beta,beta-disubstituted beta-lactones.
17 arboxylic acids to form diverse six-membered lactones.
18 tent activator of LasR than other homoserine lactones.
19 nes can lead to important four-membered beta-lactones.
20 a Kulinkovich reaction of the corresponding lactones.
21 e aliphatic polyesters from cyclic esters or lactones.
22 are typically difficult to achieve by ROP of lactones.
23 d into diastereomerically pure five-membered lactones.
24 s are easily turned into corresponding delta-lactones.
25 s (SBLs) with carbapenems also produces beta-lactones.
26 clic ethers to esters, and terminal diols to lactones.
27 for the enantioselective synthesis of gamma-lactones.
28 lides with other competing synthons of gamma-lactones.
29 e potency of 3OC(12)HSL and other homoserine lactones.
30 Ten antifouling 14-membered resorcylic acid lactones 1-10 were isolated previously with low or trace
31 ealtime detection of N-hexanoyl-L-homoserine lactone (199 Da), a gram-negative bacterial infection bi
32 ylbutanoylquinic acid, and the corresponding lactone 3-O-caffeoyl-4-O-3-methylbutanoyl-1,5-quinide, a
33 el system composed of (3-caffeoylquinic acid lactone (3-CQAL), 4- caffeoyl quinic acid lactone (4-CQA
34 s, such as N-(3-oxo-dodecanoyl)-l-homoserine lactone (3O-C12-HSL), that promote biofilm formation and
35 The cognate autoinducer, 3OC(12) homoserine lactone (3OC(12)HSL), is a more potent activator of LasR
37 ally to N-(3-hydroxydodecanoyl)-l-homoserine lactone (3OHC12-HSL) and N-(3-oxododecanoyl)-l-homoserin
38 id lactone (3-CQAL), 4- caffeoyl quinic acid lactone (4-CQAL), and 4-feruloylquinic acid lactone (4-F
39 lactone (4-CQAL), and 4-feruloylquinic acid lactone (4-FQAL)) was used for the screening of enzymes
40 sphaerides E-H (1-4) together with one gamma-lactone (5) and the methyl ester of compound 2 (11).
41 umber of variables (14 compounds), including lactones (6-pentyl-alpha-pyrone, gamma-decalactone, gamm
42 d with high monomer content of a hydrophobic lactone-accumulated in the liver and, to a lesser extent
43 of des-hydroxybilobalide is found to rely on lactone acidification through lone-pair delocalization,
44 common signaling molecule N-acyl-homoserine lactone (AHL) at concentrations 100-fold lower than the
45 which is mediated by an N-acyl L-homoserine lactone (AHL) signal (C(8)-AHL) and its cognate LuxR-typ
46 exchange of signals such as acyl-homoserine lactones (AHL) enables communication within and between
47 catalyze the biosynthesis of acyl-homoserine lactones (AHL) signals using S-adenosyl-l-methionine and
49 eleases variable chain length acylhomoserine lactones (AHLs) and acyl-oxohomoserine lactones (AOHLs)
52 es able to degrade or modify acyl-homoserine lactones (AHLs) have drawn considerable interest for the
54 m-negative bacteria are the N-acylhomoserine lactones (AHLs), which are known to affect the growth an
55 transformations include DABAL-Me(3)-mediated lactone aminolysis and a mild TBD/ethyl trifluoroacetate
56 evealed that in the case of the six-membered lactone an energetically favorable conformer adopts a ne
57 etrahydrofurans including aryl-Hagen's gland lactone analogues via intramolecular iodoetherification.
59 oducts; a tricyclic N-heterocycle-fused beta-lactone and a bicyclic enamine derived from in situ deca
60 e intact under conditions that hydrolyze the lactone and allows the ester group to be recovered when
61 s structure-activity analyses identified the lactone and diene as moieties conferring anticancer acti
62 lization has traditionally relied on lactam, lactone and disulfide bond-forming reactions that aim at
65 ernary stereocenters on structurally similar lactones and ketones, where it exhibits excellent regios
66 A strategy for the synthesis of medium-sized lactones and lactams from linear precursors is described
67 The generic statement that sesquiterpene lactones and phenolic compounds are determinants of bitt
68 bolites that included sugars, sesquiterpenes lactones and phenolics in the leaf and stem parts, which
70 , selected plant-derived five-membered gamma-lactones and six-membered delta-lactones that occur with
73 tion of the QS molecule 3-O-C(12)-homoserine lactone, and QS-regulated virulence factors pyocyanin an
75 ch as alpha,beta-unsaturated enones, esters, lactones, and lactams as well as alkenylboronic esters.
77 Enantiomerically enriched azetidines, gamma-lactones, and tetrahydroquinolines were obtained via a t
78 is involved in formation of the unsaturated lactone; and the ferric-reductase-like enzyme RbtH, whic
79 ntities of the anti-inflammatory diterpenoid lactones andrographolide and neoandrographolide, and the
80 pure bicyclo[2.2.2]octenones, including the lactone-annulated system 26, has been prepared by engagi
81 f the biosynthetic gene cluster for the beta-lactone antibiotic obafluorin and delineate its biosynth
82 erine lactones (AHLs) and acyl-oxohomoserine lactones (AOHLs) as signaling molecules during quorum se
87 sults, including the formation of a bicyclic lactone arising from oxidative termination of the photor
89 nspired by this mechanism, we exploited beta-lactones as putative mycolic acid mimics to block serine
91 steps, provides a general access to 4-alkyl lactones as well as a robust access to the target sex ph
92 of the diastereoisomers of these p-menthane lactones, as well as their common precursor, menthofuran
94 ensing inhibitor (QSI) - a N-acyl homoserine lactone autoinducer antagonist - and then dosed onto hea
95 ulted in 2,3-difunctionalized benzofuran and lactone bearing indoline-2-one scaffolds under same cond
96 ce factors, by N-3-oxododecanolyl homoserine lactone binding to the quorum sensing receptor, LasR.
100 ited greater amounts of vanillin and whiskey-lactones but lower concentrations of fruity aroma compou
101 ctions not only led to enantioenriched gamma-lactones, but also various other heterocycles and acycli
102 lectrophilicity of the alpha-methylene-gamma-lactone by replacement with an alpha-methylene-gamma-lac
104 t-chain AHLs, N-3-(oxododecanoyl)-homoserine lactone (C12-HSL) and N-butyryl homoserine lactone (C4-H
105 e lactone (C12-HSL) and N-butyryl homoserine lactone (C4-HSL), on cell viability and mucus secretion
106 ition of the RhlI product butyryl-homoserine lactone (C4-HSL), or bacteria that produce C4-HSL, to La
107 The enzymatically produced cyclopropyl-gamma-lactones can be further elaborated to furnish a variety
108 gent C-glycosidation of carbohydrate-derived lactones can be mediated by the protecting groups and ap
110 ion of various heterocyclic monomers such as lactones, carbonates, or epoxides but also to trigger th
111 vs 17 kcal mol(-1) for BTP) include its high lactone carbonyl stretching energy (1821 cm(-1) in aceto
115 imeric, trimeric, and tetrameric macrocyclic lactones consisting of units of this prostaglandin.
116 the production of the bioactive diterpenoid lactone constituents of the important medicinal herb A.
121 analytical approach we identified a fragrant lactone corresponding to an odorant zone reminiscent of
123 r esterase (HLE) hydrolyzed chlorogenic acid lactones (CQALs, FQALs) selectively, while chlorogenate
125 y active synthesis of the beta-hydroxy-gamma-lactone derivative with high enantiomeric purity using S
127 retofore unidentified alpha,beta-unsaturated lactone derived from dioxygenation of pyrene at an apica
128 building block starting from a d-gulono-1,4-lactone-derived intermediate in the current Halaven manu
129 sing two sets of chemical properties (set 1: lactone, diastase activity, sucrose - 100%) (set 2: free
135 functionalized alpha,beta-unsaturated delta-lactones featuring a CF(3)-substituted quaternary stereo
136 ent impact on C6 alcohols, volatile phenols, lactones, fermentation-derived alcohols, acids, or most
138 For the calibration curve of monacolin K (lactone form), a linear correlation in the range 6-119mi
139 orces the molecule to adopt a nonfluorescent lactone form, providing a convenient method to make fluo
145 arranges the carbon backbone, presumably via lactone-forming Baeyer-Villiger oxidation and subsequent
148 of an optically active alpha-methylene-gamma-lactone from p-chlorostyrene has been developed on the b
149 ss D SBL variants catalyze formation of beta-lactones from all clinically relevant carbapenems regard
151 leading to the formation of endocyclic enol lactones from unsaturated carboxylic acids in an one-pot
152 umarin scaffold in which the carbonyl of the lactone function of the original coumarin dyes has been
154 a catalysts provided access to bicyclic beta-lactone-fused, N-heterocycles in moderate to good yields
155 : guaiacol, cis-whisky lactone, trans-whisky lactone, gamma-nonalactone, eugenol, vanillin, and aceto
156 o use LBA as an alternative to glucono-delta-lactone (GDL) for the production of dairy gels with a co
158 s possessing the monodiene with a simplified lactone had superior anticancer efficacy relative to tax
160 ss to trifluoromethylated gamma-amino esters/lactones has been realized through the enantioselective
163 previously discovered that the sesquiterpene lactone helenalin acetate, a natural compound known to i
164 e functional groups like hydroxyl, ester, or lactone in the resultant products expand the scope of sy
165 s-conformation, and the presence of a labile lactone in this core, many synthetic methodologies commo
166 investigated an approach to decompose these lactones in a selective way without affecting the positi
167 enantiomerically enriched gamma-amino esters/lactones in good to excellent yields from the readily av
168 can overcome these challenges to yield gamma-lactones in high enantiomeric excess (up to 99%) using h
169 ith HCl provides stable gamma-NHC-bora-gamma-lactones in isolated yields ranging from 40% to 73%.
172 S molecule, N-(3-Oxododecanoyl)-L-homoserine lactone, induces candidal resistance to fluconazole by r
173 Among them, a monooxygenated, seven-membered lactone intermediate as a monodentate ligand of the iron
174 e features the construction of a crystalline lactone intermediate via a selective palladium-catalyzed
175 vel reveals that putative biosynthetic gamma-lactones intermediates are localized in the same cell ty
176 obust and scalable conversion of sugar gamma-lactones into highly valuable glycosides having a quater
180 group to form 2-carboxy-l-lyxonolactone; the lactone is hydrolyzed by a member of the amidohydrolase
187 a ubiquitin-dependent mitophagy inducer, the lactone ivermectin, we have combined genetic and imaging
188 ges were determined for nafithromycin, a new lactone-ketolide, following the completion of a nine-lab
190 ation method that is suitable for converting lactones, lactams, and cyclic ketones to their alpha,bet
191 is likely generally applicable to many other lactones, lactides, anhydrides, epoxides, and heterocumu
193 r woody/toasty, beta-damascenone and massoia lactone, likely with Z-1,5-octadien-3-one for fruit-in-s
195 ols, inulin, oligofructose and sesquiterpene lactones may be considered as potential carriers of food
197 s contributors to the widespread macrocyclic lactone (ML) resistance in several nematode species incl
198 mination of the residues of five macrocyclic lactones (MLs) (abamectin, doramectin, eprinomectin, ive
199 , the substitutions of the epoxide units and lactone moieties with cyclopropyl and lactam structural
201 n established the last stereocenter, and the lactone moiety was formed by ring-closing metathesis.
211 time, certain fatty amides, gamma- and delta-lactones of high molecular weight, and other aromatic co
212 rgent preparation of fused cyclopropyl-gamma-lactones of high value for medicinal chemistry and the s
214 s were prepared by addition of glucono-delta-lactone, once pH of 6 or 5.5 was reached, the suspension
216 acids to high value chiral hydroxy-acids and lactones poses a number of synthetic challenges: the act
219 lopropanation of the resulting bicyclic beta-lactone produces a strained housane structure that is co
220 roposelective ring opening of Bringmann-type lactones produces a product with one established axis of
221 biF1, highlighting the structure of the beta-lactone-producing thioesterase domain and an interaction
224 n with formation of an alpha-methylene-gamma-lactone proved instrumental, which had not found applica
225 es C and 30 degrees C carry N-acylhomoserine lactone quorum sensing signals, as well as alkaline phos
226 ppears to bind and sequester some homoserine lactone quorum signals, resulting in the inability of P.
229 ar Alder-ene (IMAE) reaction and a lactam-to-lactone rearrangement of tetracycle 13, a compound that
230 pulations involving the carbamate formation, lactone reduction and cyclization, afforded cyclopropyl
231 unique members isolated to date, guaianolide lactones represent a particularly prolific class of terp
232 5000 members isolated to date, sesquiterpene lactones represent a prolific source of medicinal agents
233 d pH levels by adding salt and glucono delta-lactone, respectively, to the MCC solutions prior to ren
234 the purees may be allocated to terpene- and lactone-rich ('SH-5'), ester-containing ('Criolla'), and
235 dies revealed a shift in the position of the lactone ring associated with removal of the C2-methyl an
237 nonfluorescent; however, upon opening of the lactone ring by the formation of the ethyl ester derivat
240 ntained within a highly strained 16-membered lactone ring, which also incorporates two trans-2,5-disu
241 ion, epoxide ring-opening polymerization and lactone ring-opening polymerization without requiring an
243 cts harboring 14- to 16-membered macrocyclic lactone rings to which various sugars are attached.
244 t sugar units allows the formation of unique lactone rings within the CD framework via a 1,8-HAT-beta
245 one (BTF), bearing three symmetry-equivalent lactone rings, is unique in its ability to undergo highl
246 iosynthetic intermediates of bioactive gamma-lactones rubrynolide and rubrenolide in the Amazonian tr
247 ymmetric construction of a cyclopropyl-delta-lactone scaffold at a gram scale, which could be further
248 This strategy leads to fused heterocyclic lactone scaffolds in a single step with moderate functio
249 602), only 4-vinyl-guaiacol, eugenol and cis-lactone showed odor activity values (OAV's) above 1, wit
250 nolide and a synthetic alpha-methylene-gamma-lactone showing a positive correlation between thiol rea
251 ion of a highly functionalized sesquiterpene lactone skeleton in five steps via an enantioselective k
252 the world, containing bitter sesquiterpenoid lactone (SL) compounds that may negatively affect consum
255 olecular pinacol coupling between ketone and lactone subunits to assemble the complex skeleton of (-)
256 ble molecules, specifically acyl homo serine lactones, such as N-(3-oxo-dodecanoyl)-l-homoserine lact
257 our prediction, we purified a candidate beta-lactone synthetase from Nocardia brasiliensis and recons
260 emical classes, such as aldehydes, alcohols, lactones, terpenoids, fatty aldehydes, fatty acids and h
261 table one, a derivative of the sesquiterpene lactone thapsigargin, is gradually approaching a clinica
262 trifluoroacetic acid-mediated formation of a lactone that is fused to a tetrahydrocarbazole derivativ
263 mbered gamma-lactones and six-membered delta-lactones that occur with terpenoid scaffolds are reviewe
264 logous Pd sigma-complex of the five-membered lactone the smallest Pd/endo-beta-H dihedral angle is ob
266 ectively a five-membered ring fused bicyclic lactone, the core structure present in gracilioether F.
267 catalyzing the hydrolysis of acyl-homoserine lactones; these molecules are involved in Gram-negative
268 lization converting a carboxylic acid into a lactone through the oxidation of a tertiary C-H bond und
269 controlled asymmetric synthesis of cis-gamma-lactones through a formal [3 + 2] cycloaddition of enedi
271 osa releases N-(3-oxo-dodecanoyl) homoserine lactone to suppress host immunity for its own better sur
272 tection via acid hydrolysis as well as a key lactone to tetrahydropyran conversion, in order to avoid
273 In addition, we linked the presence of those lactones to interesting odorant zones, reminiscent of mi
274 the structures of briarellin C14-C3 epsilon-lactones to new structural types containing either a C14
276 ompounds from oak wood: guaiacol, cis-whisky lactone, trans-whisky lactone, gamma-nonalactone, eugeno
279 r tetrahydropyran (THP)-fused bicyclic gamma-lactones, two privileged scaffolds often found in natura
280 s, vinyl ethers, alkenes, cyclic ethers, and lactones) under practical, inexpensive, and environmenta
281 repared from readily available dinorcholanic lactones via their reaction with 4-chlorobutyllithium fo
285 ral, 2-methoxy-4-vinylphenol and cis-whiskey lactone were the compounds that contribute the most to t
286 aled up and the alpha,beta-unsaturated delta-lactones were converted to amino acid derivatives decora
287 bi- and tricyclic, N-heterocycle-fused, beta-lactones were first synthesized in racemic fashion via t
289 nS-generated pheromone N-octanoyl homoserine lactone, which may account for the previously unexplaine
290 ations resulting in cyclopropane-fused gamma-lactones, which are key motifs found in many bioactive m
291 metric synthesis of cyclopropane-fused-delta-lactones, which are key structural motifs found in many
292 ange of epoxides can be carbonylated to beta-lactones, which are subsequently ring-opened to produce
293 situation whereby fragile substrates such as lactone will be hydrolyzed by a stronger base but will n
294 led to the identification of AJH-836, a DAG-lactone with preferential affinity for novel isozymes (n
296 were related to the aging time; cis-whiskey lactone with the type of wood pieces and octanal, 5-meth
297 ogreensporone F, 14-membered resorcylic acid lactones with a cis-2,5-disubstituted tetrahydrofuran ri
299 SQ) or methylquinidine (MeQd)) provided beta-lactones with high enantio- and diastereoselectivities.
300 three major products but with an increasing lactone yield of 33, 49, and 55% on these substrates, re