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  • 1
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 105 (1972), S. 1749-1754 
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis and Immunological Properties of Two Symmetrical Cystine Peptides with the Sequences A 14-21 and A 15-21 of the Insulin A ChainThe fully protected cystine peptides [Z-Gln-Leu-Glu(OBut)-Asn-Tyr(But)-|Cys-Asn-OBzl]2 (10) and [Z-Tyr(But)-Gln-Leu-Glu(OBut)-Asn-Tyr(But)-|Cys-Asn-OBzl]2 (11), the amino acid sequences of which correspond to sequences A 15-21 and A 14-21 of the insulin A chain, respectively, were prepared by condensation of either a penta (5)- or a heptapeptide (6) derivative via the azide with a bifunctional cystine peptide (9). These were then converted into the corresponding deblocked cystine peptide (12 or 13) by treatment with hydrogen bromide in trifluoracetic acid. The (A 14-21)2 cystine peptide (13) showed immunological activity in the passive cutaneous anaphylaxia test.
    Notes: Die vollständig geschützten Cystinpeptide [Z-Gln-Leu-Glu(OBut)-Asn-Tyr(But)-|Cys-Asn-OBzl]2 (10) bzw. [Z-Tyr(But)-Gln-Leu-Glu(OBut)-|Cys-Asn-OBzl]2 (11), deren Aminosäurefolgen den Sequenzen A 15-21 bzw. A 14-21 der Insulin-A-Kette entsprechen, wurden durch Kondensation eines Pentapeptid-Derivates (5) bzw. eines Hexapeptid-Derivates (8) über das Azid mit dem bifunktionellen Cystinpeptid (9) hergestellt und durch Behandlung mit Bromwasserstoff in Trifluoressigsäure in die schutzgruppenfreien Cystinpeptide 12 bzw. 13 übergeführt. Im Test auf passive cutane Anaphylaxie erwies sich das Cystinpeptid (A 14-21)2 (13) als immunologisch aktiv.
    Type of Medium: Electronic Resource
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  • 2
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis of Monomeric Cyclic Cystine Peptides, II. - Synthesis of the Sequence A 10-21 of Ovine Insulin as Monomeric, Cyclic, Asymmetric Cystine Peptide Derivative1)The completely protected cysteine peptide, Trt-Val-Cys(Trt)-Ser(But)-Leu-Tyr(But)-Gln-Leu-Glu(OBut)-Asn-Tyr(But)-Cys(Trt)-Asn-OBut (13), which corresponds to the amino acid series of sequence A 10-21 of the ovine insulin A-chain, was synthesized by fragment condensations. The product was then converted by treatment with iodine in methanol into the corresponding cystine peptide derivative 14 in the N-terminal free form.
    Notes: Das vollständig geschützte Cysteinpeptid Trt-Val-Cys(Trt)-Ser(But)-Leu-Tyr(But)-Gln-Leu-Glu(OBut)-Asn-Tyr(But)-Cys(Trt)-Asn-OBut (13), dessen Aminosäurefolge der Sequenz A 10-21 der Schafinsulin-A-Kette entspricht, wurde durch Fragmentkondensationen aufgebaut und durch Behandlung mit Jod in Methanol in das entsprechende Cystinpeptidderivat 14 in N-terminal freier Form übergeführt.
    Type of Medium: Electronic Resource
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