35444-44-1Relevant articles and documents
An antibody-catalyzed isomerization reaction
Uno,Ku,Prudent,Huang,Schultz
, p. 3811 - 3817 (1996)
Monoclonal antibodies (mAbs) were generated against the coplanar transition state (TS(paragraph)) analogue 1 and assayed for their ability to catalyze the isomerization of bridged biphenyls 4, 6, and 7. This is a relatively simple unimolecular reaction whose activation barrier arises from unfavorable steric interactions between the two benzylic methylene groups and strain in the bridging ring system. Seven mAbs were found that catalyzed the isomerization of 4 to 6; the most efficient (mAb 64D8E10) has k(cat) and K(M) values of 4.3 x 10-5 s-1 and 420 μM, respectively. This corresponds to a rate enhancement over the unimolecular uncatalyzed reaction (k(cat)/k(uncat)) of 2900. The dissociation constant for the TS(paragraph) analogue, K(d), was determined to be 210 nM. For both the antibody (64D8E10) catalyzed and uncatalyzed reactions, the free energy of activation (ΔG(paragraph)) is comprised largely of the enthalpy term; the antibody decreases the enthalpy of activation by 5 kcal/mol. Despite relatively large differences in the values of k(cat)/k(uncat) for the five antibodies, the ratios of K(d) to K(M)(4) are very similar. It is likely that the antibodies catalyze this reaction by reducing both ring strain and nonbonded steric interactions in the transition state.
A synthesis and properties of new 4,4-difluoro-3a,4a- diaza-s-indacene (BODIPY)-labeled lipids
Boldyrev,Molotkovsky, Jul G.
, p. 78 - 83 (2006)
A series of fluorescently labeled fatty acids of various chain lengths with 4,4-difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene-8-yl (Me 4-BODIPY-8) residue in the ω-position were synthesized. These acids were used to prepare new fluorescently labeled phosphatidylcholines, sphingomyelin, and galactosyl ceramide. The symmetry of the Me 4-BODIPY-8-fluorophore suggests that, in most bilayer membrane systems, this fluorophore would be embedded into the bilayer. Pleiades Publishing, Inc., 2006.
Synthesis of the 4-aza cyclopentenone analogue of Δ12,14-15-deoxy-PGJ2 and S-cysteine adducts
Conway, Lorna,Riccio, Anna,Santoro, M. Gabriella,Evans, Paul
, (2020)
The synthesis of a series of 4-aza cross-conjugated cyclopentenones, inspired by the natural prostaglandin Δ12,14-15-deoxy-PGJ2 (5) is described. Using the 4-aza cyclopentenone 7, the installation of the α-side chain was performed using N-functionalisation, following a Boc-deprotection. The ω-side chain was then installed through a Baylis-Hillman type aldol reaction with trans-2-octenal. This afforded 11, the aza-analogue of 5. With this prostaglandin analogue in hand, a series of thiol adducts (14–16) were prepared. Included are activities for compounds 11 and 14–16 in relation to inhibition of the transcription factor NF-κB.
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Morgan,Walton
, p. 91 (1933)
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Aziridine-2-carboxylic acid derivatives and its open-ring isomers as a novel PDIA1 inhibitors
Leite, Irena,Andrianov, Victor,Zelencova-Gopejenko, Diana,Loza, Einars,Kazhoka-Lapsa, Iveta,Domracheva, Ilona,Stoyak, Marta,Chlopicki, Stefan,Kalvins, Ivars
, p. 1086 - 1106 (2022/01/12)
[Figure not available: see fulltext.] Acyl derivatives of aziridine-2-carboxylic acid have been synthesized and tested as PDIA1 inhibitors. Calculations of charge value and distribution in aziridine ring system and some alkylating agents were performed. For the first time was found that acyl derivatives of aziridine-2-carboxylic acid are weak to moderately active PDIA1 inhibitors.
