Events The 1st International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

10.3390/ecsoc-1-02027

This submission belongs to the session a. General Organic Synthesis of the event The 1st International Electronic Conference on Synthetic Organic Chemistry

Published date

01 Sep, 1997

Citation

Esteban Pomo-Villar, Hans-Peter Weber, Gideon Shapiro, Axel Heuser, Raquel Perez Carlon, Maria del Carmen Fernandez, Encarnacion Nogueira, Synthesis of Protected Thiophospho Amino Acids for Solid Phase Peptide Synthesis, in Proceedings of The 1st International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 1997, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-1-02027

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Synthesis of Protected Thiophospho Amino Acids for Solid Phase Peptide Synthesis

Encarnacion Nogueira ¹

Maria del Carmen Fernandez ¹

Raquel Perez Carlon ¹

Axel Heuser ¹

Gideon Shapiro ¹

Hans-Peter Weber ¹

Esteban Pomo-Villar ¹

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

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

The Synthesis of (2R,5R)-2-Amino-5-Hydroxyhexanoic Acid by Intermolecular Cycloaddition

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