Insulin-Analoga mit permutiertem<i>N</i>-Terminus der A-Kette

Krail, Guntram; Brandenburg, Dietrich; Zahn, Helmut

doi:10.1515/bchm2.1975.356.s1.981

Cited by 17 publications

(2 citation statements)

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“…No literature consensus exists for the physical properties of 1 and 4 . For example, previously reported optical rotation values for 1 are −20°, −10.6°, −9.1°, −6.2°, and +20°. ,, We note that variation in both sign and magnitude is reported, despite each value being measured apparently from the same stereoisomer. The literature characterization data of 4 is similarly poor.…”

Section: Results and Discussionmentioning

confidence: 85%

Synthesis and Explosion Hazards of 4-Azido-l-phenylalanine

et al. 2018

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A reliable, scalable, cost-effective, and chromatography-free synthesis of 4-azido-L-phenylalanine beginning from L-phenylalanine is described. Investigations into the safety of the synthesis reveal that the Ullman-like Cu(I)-catalyzed azidation step does not represent a significant risk. The isolated 4-azido-L-phenylalanine product, however, exhibits previously undocumented explosive characteristics.

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Section: Results and Discussionmentioning

confidence: 85%

Synthesis and Explosion Hazards of 4-Azido-l-phenylalanine

et al. 2018

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“…The N-terminus of the B-chain was the site of selective incorporation of 125 I (Assoian & Tager, 1981;Bahrami et al, 1980). To modify insulin selectively at the B 1 phenylalanine residue (Figure 1), we first protected both A 1 and B 29 amino residues with tert-butyloxycarbonyl (Boc) groups (Krail et al, 1975;Hofmann et al, 1977Hofmann et al, , 1984. Since this reaction was extremely sensitive to reaction conditions, we studied several parameters to optimize yields in this critical step.…”

Section: Insulin Modificationmentioning

confidence: 99%

Fluorine-18 labeled insulin: a prosthetic group methodology for incorporation of a positron emitter into peptides and proteins

Shai

Kirk²,

Channing³

et al. 1989

Biochemistry

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In the present study we synthesize 18F-labeled insulin of high specific radioactivity. A new prosthetic group methodology, in which [18F]fluoride displaces a bromide group of 4-(bromomethyl)-benzoylamine intermediates, was used. The 4-(fluoromethyl)benzoyl product was chemically stable. 18F-Labeled insulin retains the essential biological properties of native insulin, as measured in vitro by binding to insulin receptors on human cells and stimulation of glucose metabolism in rat adipocytes. The overall process can be carried out speedily to yield a product of sufficient purity to permit in vivo studies. The method appears to be applicable to a wide variety of peptides.

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Insulinanaloga mit N-terminal verlängerter B-Kette

1975

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Prof. Dr. tlerman Mark zum 80. Geburtstag gewidmet (Einpangsdatum: 31. Oktober 1974) ZUSAM M FNFASSIJNG : Das nach Geiger durch selektive Hutyloxycarbonylierung von Insulin lcicht zugiingliche l\f 2 4 1 .NCH 29-Bis( ror-butyloxycarbonyl)insulin wurdc chromatographisch gercinigt und als Aminokomponente fur Peptidsynthesen mit aktiven Estern von rr.rr-Butyloxycarbonql-geschutztcn Aminosiiuren cingesetzt. Auf dicse Wcise gelang die Partialsynthese von itzB'-Lcucyl-. (;lycyl-. Lysyl-und Glutamylinsulin. Die clektrophoretisch (pH 2 und 8.6) und dunnschichtromatofraphisch einheitlichen Analoga wurden durch biologische, immunologische und C'D-spcktralc Datcn charaktcrisiert und konnten kristallisicrt werden. SUMMARY:,v,\l , ,ycH>''-Bis( rPrr-butyloxycarbony1)insulin. easily obtaincd by selective butyloxycarbonylation of insulin according to Gcigcr. was purificd by chromatography and applied as amino component for peptidc synthcscs with active esters of amino acids protected by thc butyloxycarbonyl group. By this method the partial synthesis of A""'-lcucyl-. glycyl-, lysyl-, and glutamylinsulin was achieved. The analogues showing homogeneity in electrophoresis (pH 2 and 8.6) and thin layer chromatography. wcrc charactcrired by biological. immunological. and CD-spectral data and could be crystallired.

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Insulin-Analoga mit permutiertemN-Terminus der A-Kette

Cited by 17 publications

References 0 publications

Synthesis and Explosion Hazards of 4-Azido-l-phenylalanine

Synthesis and Explosion Hazards of 4-Azido-l-phenylalanine

Fluorine-18 labeled insulin: a prosthetic group methodology for incorporation of a positron emitter into peptides and proteins

Insulinanaloga mit N-terminal verlängerter B-Kette

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