{"title":"Partial purification of a cyanobacterial membrane protein with amino terminal sequence similarity to the N-methylphenylalanine pilins.","authors":"B F Nore, M A Harrison, J N Keen, J F Allen","doi":"10.3891/acta.chem.scand.48-0578","DOIUrl":"https://doi.org/10.3891/acta.chem.scand.48-0578","url":null,"abstract":"<p><p>Cyanobacterial pilin was extracted from Synechococcus 6301 membranes using a detergent mixture comprising 1% Triton X-100, 1% Thesit and 0.5% dodecyl beta-D-maltoside. Partial purification of pilin from the crude extract was achieved by a single-step purification applying the Rotofor isoelectric focusing system. Up to 100-fold purification of pilin from the crude extract was achieved in a single run. SDS-PAGE analysis showed Synechococcus 6301 pilin migration with an apparent molecular weight of 11 kDa. The amino terminal sequence of the first 28 amino acid residues was identified. Alignment of the predicted sequence showed a 60-80% identity with amino terminal sequences of pilins from pathogenic gram-negative bacteria (enterobacteria). The apparent mass of Synechococcus 6301 pilin was, however, lower. The amino terminus of Synechococcus 6301 pilin, as with other pilins, has a high content of hydrophobic amino acids.</p>","PeriodicalId":76966,"journal":{"name":"Acta chemica Scandinavica (Copenhagen, Denmark : 1989)","volume":"48 7","pages":"578-81"},"PeriodicalIF":0.0,"publicationDate":"1994-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"18913271","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}
V Waagen, V Partali, I Hollingsaeter, M S Huang, T Anthonsen
{"title":"Stereoselectivity of Baker's yeast reduction of 2-propanones: influence of substituents.","authors":"V Waagen, V Partali, I Hollingsaeter, M S Huang, T Anthonsen","doi":"10.3891/acta.chem.scand.48-0506","DOIUrl":"https://doi.org/10.3891/acta.chem.scand.48-0506","url":null,"abstract":"<p><p>The stereoselectivity of Baker's yeast reduction of prochiral alpha-oxygenated 2-propanones has been studied by varying the substrate structure. The 1-hydroxy-3-methoxy-3-propanone 1a was reduced to the corresponding alcohol (R)-2a with 88% enantiomeric excess. Replacing the hydroxy group in 1a with phenoxy or benzyloxy (1b and 1c) gave the alcohols (S)-2b and (S)-2c with 53 and 32% ee, respectively. Reduction of the methyl ketone 1d gave the alcohol (S)-2d with 91% ee. Attempts to improve the enantioselectivity of the reduction of 1c by lowering the substrate concentration or addition of selective reductase inhibitors had only small effect on the enantioselectivity.</p>","PeriodicalId":76966,"journal":{"name":"Acta chemica Scandinavica (Copenhagen, Denmark : 1989)","volume":"48 6","pages":"506-10"},"PeriodicalIF":0.0,"publicationDate":"1994-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"19054834","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}
L Ding, L Grehn, E De Clercq, G Andrei, R Snoeck, J Balzarini, B Fransson, U Ragnarsson
{"title":"Synthesis and antiviral activity of three pyrazole analogues of distamycin A.","authors":"L Ding, L Grehn, E De Clercq, G Andrei, R Snoeck, J Balzarini, B Fransson, U Ragnarsson","doi":"10.3891/acta.chem.scand.48-0498","DOIUrl":"https://doi.org/10.3891/acta.chem.scand.48-0498","url":null,"abstract":"<p><p>The synthesis of three new monopyrazole analogues of the antiviral compound distamycin A is reported. Suitably protected 4-amino-1-methylpyrrole-2-carboxylic acid and 3-amino-1-methylpyrazole-5-carboxylic acid derivatives were chosen as starting materials. The construction of the trimeric polyamide framework was accomplished by assembly of the monomeric precursors under condensing conditions by analogy with our previous methodology, although with significant improvements in some pivotal steps. After chromatographic purification and spectroscopic characterisation, the analogues were assayed for antiviral activity. Compounds 7a-c inhibited vaccinia virus at a concentration similar to or lower than distamycin A and the related antibiotic netropsin. Analogues 7b and 7c exhibited an antiviral effect comparable to those of distamycin A and netropsin against HSV-1 and HSV-2, whereas their antiviral activity against several other viruses including HIV-1 and HIV-2 was somewhat lower. The cellular toxicity of 7a-c toward different host cell types proved to be of similar magnitude or lower than those of distamycin A and netropsin.</p>","PeriodicalId":76966,"journal":{"name":"Acta chemica Scandinavica (Copenhagen, Denmark : 1989)","volume":"48 6","pages":"498-505"},"PeriodicalIF":0.0,"publicationDate":"1994-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"19054833","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":"Sequence-selective metal ion binding to DNA hexamers.","authors":"S Steinkopf, E Sletten","doi":"10.3891/acta.chem.scand.48-0388","DOIUrl":"https://doi.org/10.3891/acta.chem.scand.48-0388","url":null,"abstract":"<p><p>Base-selective interaction between divalent metal ions and DNA oligomers has been studied by 1D and 2D NMR spectroscopy. Titration with paramagnetic metal ions induces selective line broadening of resonances from protons close to the binding site. Also the intensities of 2D NOESY cross-peaks involving paramagnetic affected protons will be quenched. Two hexamers, 5'-d(CGTACG)2 (I) and 5' (GCATGC)2 (II) have been titrated with Mn(II) ions. Manganese binds selectively to the terminal guanine, G1, in sequence II as manifested through pronounced paramagnetic line broadening and loss of intensities of NOESY cross-peaks involving G-H8 protons. The second guanine, G5, and the non-guanine residues are appreciably less affected. In sequence I both guanines, G2 and G6, are the targets for selective metal binding as judged from G-H8 line broadening. The extent of interaction is almost identical for the two G-residues and comparable to that observed for G1 in sequence II. The metal binding site in the duplexes is most likely nitrogen G-N7. Selective metal binding to oligonucleotides may be related to sequence-dependent variation in molecular electrostatic potentials (MEP) along the chain.</p>","PeriodicalId":76966,"journal":{"name":"Acta chemica Scandinavica (Copenhagen, Denmark : 1989)","volume":"48 5","pages":"388-92"},"PeriodicalIF":0.0,"publicationDate":"1994-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"19012618","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}
C Rivera Baeza, K Kask, U Langel, T Bartfai, A Undén
{"title":"Analogs of galanin (1-16) modified in positions 1-3 as ligands to rat hypothalamic galanin receptors.","authors":"C Rivera Baeza, K Kask, U Langel, T Bartfai, A Undén","doi":"10.3891/acta.chem.scand.48-0434","DOIUrl":"https://doi.org/10.3891/acta.chem.scand.48-0434","url":null,"abstract":"<p><p>Structure-activity relationship (SAR) studies have revealed that the first three residues of galanin (Gly1-Trp2-Thr3) are of critical importance for high-affinity binding to the galanin receptor. Furthermore degradation studies have shown that galanin is easily cleaved to yield inactive fragments in rat hypothalamus (t1/2 = 100 min). To obtain galanin receptor ligands with long-lasting biological activity the amino-terminus of galanin must be protected. We have therefore synthesized analogs of rat galanin(1-16) carrying modifications at the three amino-termini of galanin. All modifications of the peptide backbone flanking Trp2 as in the analogs [N-Me-Trp2]-galanin(1-16), [Tcc2]-galanin-(1-16), (Trp2-psi[CH2NH]-Thr3)-galanin-(1-16) produced a dramatic loss of affinity toward the galanin receptor. [N-Me-Thr3]-galanin(1-16) was the most active of the peptide backbone modified analogs (KD = 997 +/- 1 nM). Modifications of the indole ring in Trp2 ([For-Trp2]-galanin-(1-16), [Tcc2]-galanin-(1-16)) yielded analogs which, at concentrations up to 10 microM, did not displace [125I]galanin binding. N-Methylation of Gly1 by the introduction of sarcosine ([Sar1]-galanin(1-16)) did not significantly affect the ligand-binding properties of galanin(1-16) (KD = 8.7 +/- 0.1 nM).</p>","PeriodicalId":76966,"journal":{"name":"Acta chemica Scandinavica (Copenhagen, Denmark : 1989)","volume":"48 5","pages":"434-8"},"PeriodicalIF":0.0,"publicationDate":"1994-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"19012619","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 the 2\"-hydroxy, 4\"-deoxy and 4\"-epi analogues of beta-D-GalNAc-(1-->3)-alpha-D-Gal-(1-->4)-beta-D-Gal, the terminal trisaccharide of globotetraose.","authors":"U Nilsson, A Wendler, G Magnusson","doi":"10.3891/acta.chem.scand.48-0356","DOIUrl":"https://doi.org/10.3891/acta.chem.scand.48-0356","url":null,"abstract":"<p><p>Radical deoxygenation of methyl 3,6-di-O-benzoyl-2-deoxy-4-O-imidazol-1-yl-thiocarbonyloxy-2-phtha limido-beta-D - glucopyranoside 5 gave methyl 3,6-di-O-benzoyl-2,4-dideoxy-2-phthalimido-beta-D-glucopyranoside 6, which was converted into the corresponding methyl thioglycoside donor 9. Methylsulfenyl trifluoromethane-sulfonate-promoted glycosylation of 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-benzyl-alpha-D-galactopyranosyl)-bet a-D- galactopyranoside 10, followed by removal of protecting groups gave the 4\"-deoxy analogue 12 of the terminal trisaccharide of globotetraose. Silver trifluoromethanesulfonate-promoted glycosylation of the same disaccharide alcohol 10 with 3,4,6-tri-O-acetyl-2-deoxy-2- phthalimido-alpha/beta-D-glucopyranosyl bromide 13 and 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl bromide 16, followed by deblocking, gave the 2\"-hydroxy and 4\"-epi analogues 15 and 18, respectively.</p>","PeriodicalId":76966,"journal":{"name":"Acta chemica Scandinavica (Copenhagen, Denmark : 1989)","volume":"48 4","pages":"356-61"},"PeriodicalIF":0.0,"publicationDate":"1994-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"19020557","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":"Facile preparation of 1,6-anhydrohexoses using solvent effects and a catalytic amount of a Lewis acid.","authors":"P M Aberg, B Ernst","doi":"10.3891/acta.chem.scand.48-0228","DOIUrl":"https://doi.org/10.3891/acta.chem.scand.48-0228","url":null,"abstract":"<p><p>Refluxing solutions of monosaccharides, unprotected at the 6-position and carrying O-methyl, S-ethyl, O-acetyl and OH-groups at the anomeric center, in acetonitrile containing a catalytic amount of a Lewis acid (O.1-0.4 equiv.) yielded 1,6-anhydrohexopyranoses in good to high yields. Best results were obtained with methyl 2,3,4-tri-O-dideuteriobenzyl-alpha-D-glycosides (87-91%). Dideuteriobenzyl protective groups were used to facilitate NMR spectral interpretations.</p>","PeriodicalId":76966,"journal":{"name":"Acta chemica Scandinavica (Copenhagen, Denmark : 1989)","volume":"48 3","pages":"228-33"},"PeriodicalIF":0.0,"publicationDate":"1994-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"19147096","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}
N Berova, J Breinholt, G W Jensen, A Kjaer, L C Lo, K Nakanishi, R I Nielsen, C E Olsen, C Pedersen, C E Stidsen
{"title":"Malonofungin: an antifungal aminomalonic acid from Phaeoramularia fusimaculans.","authors":"N Berova, J Breinholt, G W Jensen, A Kjaer, L C Lo, K Nakanishi, R I Nielsen, C E Olsen, C Pedersen, C E Stidsen","doi":"10.3891/acta.chem.scand.48-0240","DOIUrl":"https://doi.org/10.3891/acta.chem.scand.48-0240","url":null,"abstract":"<p><p>In screening for antifungal metabolites, a novel compound, malonofungin, exhibiting growth inhibitory activity against Botrytis cinerea (grey mould), has been isolated from fermentations of Phaeoramularia fusimaculans CBS 616.87. Its structure is established as (E)-(3R,4S,5S)-5-acetoxy-2-amino-2-carboxy-3,4-dihydroxy-14-oxoicos++ +-6-enoic acid, representing an addition to the rare class of naturally occurring aminomalonic acids. 1H NMR data and extensive use of CD spectroscopy have been utilized to establish the absolute stereochemistry of malonofungin. The structural and biological relationship of malonofungin to previously reported fungal metabolites is discussed.</p>","PeriodicalId":76966,"journal":{"name":"Acta chemica Scandinavica (Copenhagen, Denmark : 1989)","volume":"48 3","pages":"240-51"},"PeriodicalIF":0.0,"publicationDate":"1994-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"19147097","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":"5'-Azido and 5'-fluoro alpha-nucleosides as analogues of AZT and FLT.","authors":"L Schmidt, E B Pedersen, C Nielsen","doi":"10.3891/acta.chem.scand.48-0215","DOIUrl":"https://doi.org/10.3891/acta.chem.scand.48-0215","url":null,"abstract":"<p><p>5-Azido-2,5-dideoxy-beta-D-erythro-pentofuranosyl nucleosides 10 and their corresponding alpha-anomers 11 have been synthesized by condensation of methyl 3-O-acetyl-5-azido-2,5-dideoxy-beta-D-erythro-pentofuranoside (7) with silylated nucleobases followed by deprotection with methanolic ammonia. Reaction of silylated thymine (19) with methyl 2,3-di-O-benzoyl-5-deoxy-5-fluoro-D-arabino-pentofuranoside (15) and methyl 5-azido-2,3-di-O-benzoyl-5-deoxy-alpha-D-arabino-pentofuranoside (17 alpha) afforded a mixture of the alpha-nucleosides 20 and the acyclo nucleosides 5-fluoro- and 5-azido-2,3-O-dibenzoyl-5-deoxy-1-O-methyl-1-(thymin-1-yl)-D -arabinitol (22). Compounds 20 and 22 were deprotected with methanolic ammonia to give the acyclic nucleosides 21 and 23, respectively. The new nucleosides were inactive against HSV-1 and HIV-1.</p>","PeriodicalId":76966,"journal":{"name":"Acta chemica Scandinavica (Copenhagen, Denmark : 1989)","volume":"48 3","pages":"215-21"},"PeriodicalIF":0.0,"publicationDate":"1994-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"19147212","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":"HPLC and NMR investigation of the serum amine oxidase catalyzed oxidation of polyamines.","authors":"G Houen, K Bock, A L Jensen","doi":"10.3891/acta.chem.scand.48-0052","DOIUrl":"https://doi.org/10.3891/acta.chem.scand.48-0052","url":null,"abstract":"<p><p>In the presence of amine oxidases polyamines arrest cell proliferation owing to the generation of hydrogen peroxide and amino aldehydes. In this investigation the bovine serum amine oxidase catalyzed oxidation of polyamines has been studied by HPLC analysis of dansylated reaction products with or without NaBH4 reduction and by NMR spectroscopy of the reaction products and 3-aminopropanal was found to be a major reaction product. These findings were further substantiated by analysis of the reaction products by ion-exchange chromatography and by analysis of the products formed by oxidation of polyamines by the cofactor of Cu amine oxidases, 6-hydroxydopa. 3-Aminopropanal is unstable and can give rise to acrolein by beta-elimination.</p>","PeriodicalId":76966,"journal":{"name":"Acta chemica Scandinavica (Copenhagen, Denmark : 1989)","volume":"48 1","pages":"52-60"},"PeriodicalIF":0.0,"publicationDate":"1994-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"19121998","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}