{"title":"The solubilities of denatured proteins in different organic solvents.","authors":"G Houen, C Svaerke, V Barkholt","doi":"10.3891/acta.chem.scand.53-1122","DOIUrl":"https://doi.org/10.3891/acta.chem.scand.53-1122","url":null,"abstract":"<p><p>The solubilities of heat-denatured and reduced, S-carboxymethylated proteins have been investigated in various organic solvents. Polar, protic solvents (formic acid, trifluoroacetic acid, 3-mercaptopropionic acid) were found to be good solvents for the denatured proteins (20-40 mg ml-1), and the solubilities of the reduced, S-carboxymethylated proteins were generally higher than those of the heat-denatured forms. Most other organic solvents were less effective in solubilizing the denatured proteins. Apolar solvents did not solubilise denatured proteins, but low solubilizing powers were observed for polar, aprotic solvents. Heat-denaturation was observed to result in the formation of large intermolecular aggregates, which, for ovalbumin and lysozyme, were formed by intermolecular S-S bonds, but for bovine serum albumin involved intermolecular isopeptide bonds.</p>","PeriodicalId":76966,"journal":{"name":"Acta chemica Scandinavica (Copenhagen, Denmark : 1989)","volume":"53 12","pages":"1122-6"},"PeriodicalIF":0.0,"publicationDate":"1999-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"21486352","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
B Långström, T Kihlberg, M Bergström, G Antoni, M Björkman, B H Forngren, T Forngren, P Hartvig, K Markides, U Yngve, M Ogren
{"title":"Compounds labelled with short-lived beta(+)-emitting radionuclides and some applications in life sciences. The importance of time as a parameter.","authors":"B Långström, T Kihlberg, M Bergström, G Antoni, M Björkman, B H Forngren, T Forngren, P Hartvig, K Markides, U Yngve, M Ogren","doi":"10.3891/acta.chem.scand.53-0651","DOIUrl":"https://doi.org/10.3891/acta.chem.scand.53-0651","url":null,"abstract":"<p><p>Some examples of recent development of the synthesis of compounds labelled with short-lived beta(+)-emitting radionuclides will be discussed with an emphasis on the importance of time in selecting a synthetic strategy. Furthermore the use of such labelled compounds to monitor certain processes in areas within the field of analytical chemistry and in various applications in drug development will be presented.</p>","PeriodicalId":76966,"journal":{"name":"Acta chemica Scandinavica (Copenhagen, Denmark : 1989)","volume":"53 9","pages":"651-69"},"PeriodicalIF":0.0,"publicationDate":"1999-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"21350094","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Hydrolysis of organophosphorus nerve agent soman by the monoclonal antibodies elicited against an oxyphosphorane hapten.","authors":"J Yli-Kauhaluoma, T Humppi, A Yliniemelä","doi":"10.3891/acta.chem.scand.53-0473","DOIUrl":"https://doi.org/10.3891/acta.chem.scand.53-0473","url":null,"abstract":"<p><p>The antibody-mediated hydrolysis of the nerve agent O-1,2,2-trimethylpropyl methylphosphonofluoridate (soman) 1 has now been established with two monoclonal antibodies raised against the cyclic pentacovalent methyloxyphosphorane hapten 10 that mimics the pentacoordinated trigonal bipyramidal transition-state of the reaction. The hydrolysis reaction was studied using molecular orbital methods at the MP2/6-31 + G*/(/)HF/6-31 + G* level of accuracy. According to the ab initio calculations, the reaction seems to proceed via three separate transition-states. The calculations are in good agreement with the experimental results. The 1,3-dioxabenzophosphole hapten 10 was synthesized, coupled to the carrier protein and the antibodies were obtained by the hybridoma technique. Two antibodies, DB-108P and DB-108Q were found to enhance the rate of soman hydrolysis and they were kinetically characterised.</p>","PeriodicalId":76966,"journal":{"name":"Acta chemica Scandinavica (Copenhagen, Denmark : 1989)","volume":"53 7","pages":"473-9"},"PeriodicalIF":0.0,"publicationDate":"1999-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"21289876","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Preparation and antimicrobial studies of acyclic sulfamates.","authors":"H S Gautun, T Bergan, P H Carlsen","doi":"10.3891/acta.chem.scand.53-0446","DOIUrl":"https://doi.org/10.3891/acta.chem.scand.53-0446","url":null,"abstract":"<p><p>A series of acyclic sulfamates have been prepared and tested for antimicrobial activity. Thus, the oxysulfonyl isocyanates, ROSO2NCO (1a, R = 4-methoxyphenyl; 1b, R = phenyl; 1c, R = 4-chlorophenyl and 1d, R = 2,2,2-trifluoroethyl) have been prepared in 76-91% yield from chlorosulfonyl isocyanate. Treatment of 1a-d with glycidol gave the glycidyl carbamates 2a d. Internal cyclisation afforded the corresponding 4-hydroxymethyl-2-oxazolidinones 3a-d, which in turn were hydrolysed to give the free amino alcohols 4a-d. The yields were in the range 39-85%. A preliminary agar diffusion test of 2a-d, 3a-d, 4a-d indicated 2a-d and 3c to be possible antimicrobial agents. A more thorough analysis of these compounds revealed a minimum inhibition concentration (MIC) of 128 and 64 mg l-1 for glycidyl p-methoxyphenoxysulfonylcarbamate (2a) and glycidyl phenoxysulfonylcarbamate (2b) respectively, against Branhamella catarrhalis.</p>","PeriodicalId":76966,"journal":{"name":"Acta chemica Scandinavica (Copenhagen, Denmark : 1989)","volume":"53 6","pages":"446-52"},"PeriodicalIF":0.0,"publicationDate":"1999-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"21246119","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Syntheses of some polyunsaturated sulfur- and oxygen-containing fatty acids related to eicosapentaenoic and docosahexaenoic acids.","authors":"S Flock, M Lundquist, L Skattebøl","doi":"10.3891/acta.chem.scand.53-0436","DOIUrl":"https://doi.org/10.3891/acta.chem.scand.53-0436","url":null,"abstract":"<p><p>With the aim of enhancing selectively the beneficial biological effects of eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) a number of polyunsaturated fatty acids containing sulfur or oxygen atoms in the chain has been synthesized starting from EPA and DHA, respectively. Oxidative degradation of these acids led to the corresponding aldehydes all-(Z)-3,6,9,12-pentadecatetraenal and all-(Z)-3,6,9,12,15-octadecapentaenal. Reactions with DBU converted these aldehydes quantitatively into the conjugated isomers (2E,6Z,9Z,12Z)-pentadecatetraenal and (2E,6Z,9Z,12Z,15Z)-octadecapentaenal, respectively. The four aldehydes were transformed by a sequence of reactions comprising reduction to the alcohols, halogenation and substitution with mercapto esters into the corresponding sulfur containing polyunsaturated fatty acid esters. The oxygen containing esters were prepared from the respective alcohol by boron trifluoride catalysed reaction with ethyl diazoacetate.</p>","PeriodicalId":76966,"journal":{"name":"Acta chemica Scandinavica (Copenhagen, Denmark : 1989)","volume":"53 6","pages":"436-45"},"PeriodicalIF":0.0,"publicationDate":"1999-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"21246118","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
T Anthonsen, B H Hoff, N U Hofsløkken, L Skattebøl, E Sundby
{"title":"Synthesis of 1,3-dithianes and 1,3-dithiolanes. Baker's yeast reduction and lipase-catalyzed resolution for synthesis of enantiopure derivatives.","authors":"T Anthonsen, B H Hoff, N U Hofsløkken, L Skattebøl, E Sundby","doi":"10.3891/acta.chem.scand.53-0360","DOIUrl":"https://doi.org/10.3891/acta.chem.scand.53-0360","url":null,"abstract":"<p><p>Three 1,3-dithiolanes and four 1,3-dithianes have been synthesised from 1-(1,3-dithiolan-2-yl)-2-propanone and 1-(1,3-dithian-2-yl)-2-propanone, respectively. Asymmetric reductions of these ketones using baker's yeast gave the corresponding enantiopure (S)-alcohols. Baker's yeast also reduced the double bond in 3-(1,3-dithian-2-yl)-3-buten-2-one enantioselectively to give (S)-3-(1,3-dithian-2-yl)-2-butanone. 3-(1,3-Dithian-2-yl)-3-buten-2-one was also reduced chemo-selectively and the resulting 3-(1,3-dithian-2-yl)-3-buten-2-ol was resolved by transesterification in organic solvent using lipase B from Candida antarctica to yield the (S)-alcohol and the (R)-acetate with very high enantiomeric ratio, E. Racemic 1-(1,3-dithiolan-2-yl)-2-propanol and 1-(1,3-dithian-2-yl)-2-propanol were also resolved under similar conditions to give the (S)-alcohols and the corresponding (R)-acetates.</p>","PeriodicalId":76966,"journal":{"name":"Acta chemica Scandinavica (Copenhagen, Denmark : 1989)","volume":"53 5","pages":"360-5"},"PeriodicalIF":0.0,"publicationDate":"1999-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"21222763","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Liquid junction potential in potentiometric titrations. 5. Deduction of the potential functions for E.M.F. cells with complex formation and with liquid junctions of the type AY [symbol: see text] AY + BYz(B) + HY + AyL.","authors":"E Néher-Neumann","doi":"","DOIUrl":"","url":null,"abstract":"<p><p>Equations were derived, in a general form, for the calculation of the total cell e.m.f. for cells containing liquid junctions of constant ionic medium type, where formation of strong complexes takes place. The total cell e.m.f. is: EJ = E0J + (g/zJ) log cJfJTS2 + ED + EDf Here, (A+, Y-) is the ionic medium, J is the potential-determining ion, Bz(B)+ is the central metal ion, ED is the ideal diffusion potential (Henderson term), EDf is the contribution of the activity coefficients to the diffusion potential, AyL is the ligand. fJTS2 denotes the activity coefficients in the terminal solution TS2. The concentration of a chosen ion of the ionic medium, C, should be in the range 0.5 < or = C < or = 3 mol dm-3. The charge of the metal ion Bz(B)+ should be < or = 3. The total potential anomalies in the cells are delta EJ = (g/zJ) log fJTS2 + ED + EDf</p>","PeriodicalId":76966,"journal":{"name":"Acta chemica Scandinavica (Copenhagen, Denmark : 1989)","volume":"53 5","pages":"314-9"},"PeriodicalIF":0.0,"publicationDate":"1999-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"21222762","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Synthesis of a boronated naphthalimide for potential use in boron neutron capture therapy (BNCT).","authors":"H Ghaneolhosseini, S Sjöberg","doi":"10.3891/acta.chem.scand.53-0298","DOIUrl":"https://doi.org/10.3891/acta.chem.scand.53-0298","url":null,"abstract":"","PeriodicalId":76966,"journal":{"name":"Acta chemica Scandinavica (Copenhagen, Denmark : 1989)","volume":"53 4","pages":"298-300"},"PeriodicalIF":0.0,"publicationDate":"1999-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"21085312","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Stereochemical variations on the colchicine motif. Part 4. A remote metalation approach toward a colchicine analog with a five-membered B-ring.","authors":"U Berg, H Bladh","doi":"10.3891/acta.chem.scand.52-1380","DOIUrl":"https://doi.org/10.3891/acta.chem.scand.52-1380","url":null,"abstract":"<p><p>Attempts to prepare a colchicine analog with a 5-membered B-ring by remote metalation of N,N-diethyl-3,4,5-trimethoxy-2-(5'-methoxy-4'-oxo-2', 5',7'-cycloheptatrienyl)-benzamide (2) led to ring contraction of the methoxytropone ring to the p-methoxycarbonylphenyl derivative (3). Dynamic 1H NMR investigations showed that the biaryl amide 2 exists as a mixture of diastereomers due to hindered rotation around both aryl-aryl and aryl-amide bonds, with rotational barriers of ca. 63 kJ mol-1. The colchicine and allocolchicine analogs 2 and 3 do not notably affect tubulin polymerization, despite the structural similarities with active analogs. The reduced tubulin binding activity of 2 and 3 may be a result of increasing steric bulk.</p>","PeriodicalId":76966,"journal":{"name":"Acta chemica Scandinavica (Copenhagen, Denmark : 1989)","volume":"52 12","pages":"1380-5"},"PeriodicalIF":0.0,"publicationDate":"1998-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"20788300","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"1-Azaribofuranoside analogues as designed inhibitors of purine nucleoside phosphorylase. Synthesis and biological evaluation.","authors":"S U Hansen, M Bols","doi":"10.3891/acta.chem.scand.52-1214","DOIUrl":"https://doi.org/10.3891/acta.chem.scand.52-1214","url":null,"abstract":"<p><p>Pyrrolidine analogues of 2-deoxyribofuranose, having nitrogen in place of anomeric carbon, have been synthesised as potential transition state analogues of enzymatic nucleoside cleavage. Efficient synthetic methods were developed that allowed the synthesis of a wide range of 4-substituted 3-hydroxypyrrolidines starting from pyrroline and using opening of the pyrrolidine 3,4-epoxide, with carbon nucleophiles. Among the compounds synthesised were the 4-cyano- [(+/-)-16], 4-hydroxymethyl [(+/-)-22] and 4-carboxymethyl derivates [(+/-)-18]. From the hydroxymethyl derivative [(+/-)-22] N-alkylation with chloromethyluracil gave an inosine analogue [(+/-)-23]. The new compounds were tested for inhibition of human erythrocyte purine nucleoside phosphorylase. Compound (+/-)-22 was found to show non-competitive inhibition of the enzyme with a Ki of 160 microM. This suggested that (+/-)-22 binds to the ribofuranose portion of the active site. Furthermore, a solid-phase synthesis of 1'-azanucleoside analogues was developed.</p>","PeriodicalId":76966,"journal":{"name":"Acta chemica Scandinavica (Copenhagen, Denmark : 1989)","volume":"52 10","pages":"1214-22"},"PeriodicalIF":0.0,"publicationDate":"1998-10-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"20696916","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}