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Solid phase synthesis of a tetrapeptide labelled with Carbon-13. Preparation of L-[U-13C]lysyl-L-[1-13C]arginyl-L-[3-13C]asparyl-L-[1-13C]serine

✍ Scribed by Thierry Humbert; Alain Marsura; Cuong Luu-Duc

Publisher
John Wiley and Sons
Year
1992
Tongue
French
Weight
881 KB
Volume
31
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

Synthesis of a [^13^C] tetrapeptide L‐[U‐^13^C]Lysyl‐L‐[1‐^13^C]Arginyl‐L‐[3‐^13^C]Aspartyl‐L‐[1‐^13^C] Serine (KRDS) on a p‐alkoxybenzyl ester polystyrene‐1% divinylbenzene resin support is described by using repetitive nonhydrolytic base cleavage of α‐amino protective groups in Solid Phase Peptide Synthesis (SPPS). Protected [^13^C] amino acid (AA) used in this SPPS model were prepared with 9‐Fluorenylmethyloxycarbonyl (Fmoc) protecting group and with different acid labile side chain protecting group over AA type as: Fmoc‐Ser(tert‐Bu)‐OH, Fmoc‐Asp(tert‐Bu)‐OH, Fmoc‐Arg(Pmc)‐OH and Fmoc‐Lys(Fmoc)‐OH. All the protected AA were coupled by N,N′‐dicyclohexyl carbodiimide (DCC) procedure, followed by Fmoc group cleavage using 20% piperidine in N,N dimethylacetamide (DMA). Quantitative deblocking side‐chain AA protection and removal of KRDS from the solid support was effected by treatment with 50% trifluoroacetic acid in methylene chloride in a one pot‐procedure. Homogeneous free [^13^C] KRDS was obtained in 90% overall yield after HPLC purification. This synthesis schedule offered the advantage over present solid phase method which used acidolysis for repetitive α‐amino group deblocking.

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