Synthesis of Protected Thiophospho Amino Acids for Solid Phase Peptide Synthesis

Encarnacion Nogueira; Maria del Carmen Fernandez; Raquel Carlon; Axel Heuser; Gideon Shapiro; Hans-Peter Weber; Esteban Pomo-Villar

doi:10.3390/ecsoc-1-02027

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Microwave Application in Organic Synthesis. Microwave-Assisted Preparation of Diphenylamines in 'Dry Media'

Synthesis of Protected Thiophospho Amino Acids for Solid Phase Peptide Synthesis

Encarnacion Nogueira

Maria del Carmen Fernandez

Raquel Perez Carlon

Axel Heuser

Gideon Shapiro

Hans-Peter Weber

Esteban Pomo-Villar

¹ Preclinical Research, Novartis Pharma Ltd., CH-4002 Basel, Switzerland

Published: 01 September 1997 by MDPI in The 1st International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-1-02027

Abstract: The synthesis of protected thiophospho amino acids, either as thiophosphotriesters or -diesters, conceived as building blocks for solid-phase synthesis of thiophosphorylated peptides is described. The thiophosphotriesters 4-9, namely O,O-diprotected, -thiophosphorylated N-Alloc, N-Fmoc and N-Boc protected serine, threonine and tyrosine, were prepared in a one-pot procedure from the corresponding N-protected amino acids. From O,O-dibenzyl N-Fmoc serine thiophosphate 7, either S-benzyl (10) or O-benzyl (11) thiophosphodiesters can be obtained.

Keywords: Thiophospho Amino acids

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