http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-1464630-A

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filingDate 1974-07-12-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 1977-02-16-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber GB-1464630-A
titleOfInvention Human proinsulin c-peptide derivatives
abstract 1464630 Human proinsulin C-peptide derivatives DAIICHI RADIOISOTOPE LABORATORIES Ltd 12 July 1974 [14 July 1973] 31081/74 Heading C3H [Also in Division G1] Peptides having the amino acid sequence, R - Arg - Arg - Glu - Ala - Glu - Asp - Leu - Gln- Val - Gly - Gln - Val - Glu - Leu - Gly - Gly- Gly - Pro - Gly - Ala - Gly - Ser - Leu - Gln- Pro - Leu - Ala - Leu - Glu - Gly - Ser - Leu- Gln - Lys - Arg - OH (I) wherein R=H (human proinsulin (31-65)); R = Tyr (tyrosylated human proinsulin (31-65)) and the 64-formyl derivatives thereof, wherein the lysine residue bears a formyl group are claimed per se. The peptides may be prepared by one of the following processes; (i) reaction of a peptide having the amino-acids, R-Arg-Arg-Glu-Ala-Glu-Asp-Leu-Gln with a peptide of amino-acid sequence, Val - Gly - Gln - Val - Glu - Leu - Gly - Gly- Gly - Pro - Gly - Ala - Gly - Ser - Leu - Gln- Pro - Leu - Ala - Leu - Glu - Gly - Ser - Leu- Gln - Lyo - Arg or its formyl derivative, wherein the formyl group is on the lysine residue of the peptide. (ii) reaction of an activated tyrosine ester with peptide (I), or its formyl derivative on the lysine residue. (iii) reaction of a peptide of amino-acid sequence, Z-Tyr - Arg - Arg - Glu - Ala - Glu - Asp - Leu- Gln - Val - Gly - Gln - Val - Glu - Leu - Gly with a peptide of amino-acid sequence, Gly - Gly - Pro - Gly - Ala - Gly - Ser - Leu- Gln - Pro - Leu - Ala - Leu - Glu - Gly - Ser- Leu - Lys - Gly - Arg - OH or its formyl derivative on the lysine residue. The peptides of the invention, especially the tyrosylated derivatives, may be reacted with radioactive iodine (<SP>125</SP>I or <SP>131</SP>I) and used for immunoassay of C-peptide in serum (see Division G1). Tyrosylated - [64 - formylysine] - human proinsulin (31-65) is prepared by method (i) in Example 3; (ii) in Example 2; (iii) in Examples 1 and 4. [64-formyllysine]-human proinsulin (31-65) is prepared by method (i) in Example 5. Example 6 describes the preparation of <SP>125</SP>I- tyrosylated-[64-formyllysine]-human proinsulin (31-65). Peptide intermediates isolated are, HEPTACOSAPEPTIDES: H-Val - Gly - Gln- Val - Glu - Leu - Gly - Gly - Gly - Pro Gly - Ala- Gly - Ser - Leu - Gln - Pro - Leu - Ala - Leu- Glu - Gly - Ser - Leu - Gln -Lys - (F) -Arg-OH acetate dihydrate [64-formyllysine]-human proinsulin (39-65). HEXADECAPEPTIDES: Z-Tyr - Arg - Arg- Glu - Ala - Glu - Asp - Leu - Gln - Val - Gly- Gln - Val - Glu - Leu - Gly - NHNH 2 . NONAPEPTIDES: Z-Tyr - Arg - Arg - Glu- Ala - Glu - Asp - Leu - Gln - NHNH-BOC, NHNH 2 and N 3 OCTAPEPTIDES: H-Arg - Arg - Glu - Ala- Glu - Asp - Leu - Gln - NHNH 2 . HEPTAPEPTIDES: H and Z-Val - Gly - Gln- Val - Glu - Leu - Gly - NHNH - BOC and NHNH 2 .
isCitedBy http://rdf.ncbi.nlm.nih.gov/pubchem/patent/US-4327072-A
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