Synthesis of Fmoc- and Boc-Protected (2S,5S)- and (2R,5R)-5-Aminomethylprolines

Bartuschat A, Hegmann N, Heinrich M (2019)

Publication Type: Journal article

Publication year: 2019

Journal

Synthesis-Stuttgart Thieme Publishing / Georg Thieme Verlag

Book Volume: 51

Pages Range: 976-984

Journal Issue: 4

DOI: 10.1055/s-0037-1610304

Abstract

The proline derivatives (2S, 5S) dmamPro, (2S, 5S) N-Boc-amPro and (2R, 5R) dmamPro are useful building blocks for peptides since they allow conformational fixation of peptidyl-CO-N-prolyl bonds in the unusual cis conformation. The stereoselective syntheses of these dimethylaminomethyl- prolines is achieved from literature-known precursors with overall yields of 23% [over 8 steps for (2S, 5S) dmamPro], 33% [over 9 steps for (2S, 5S) N-Boc-amPro] and 12% [over 8 steps for (2R, 5R) dmamPro]. The applicability of (2S, 5S) N-Boc-amPro in peptide synthesis is demonstrated through the preparation of an Fmoc-Val-amPro- OMe dipeptide.

Authors with CRIS profile

Amelie Bartuschat Professur für Pharmazeutische Chemie Nina Hegmann Professur für Pharmazeutische Chemie Markus Heinrich Professur für Pharmazeutische Chemie

How to cite

APA:

Bartuschat, A., Hegmann, N., & Heinrich, M. (2019). Synthesis of Fmoc- and Boc-Protected (2S,5S)- and (2R,5R)-5-Aminomethylprolines. Synthesis-Stuttgart, 51(4), 976-984. https://dx.doi.org/10.1055/s-0037-1610304

MLA:

Bartuschat, Amelie, Nina Hegmann, and Markus Heinrich. "Synthesis of Fmoc- and Boc-Protected (2S,5S)- and (2R,5R)-5-Aminomethylprolines." Synthesis-Stuttgart 51.4 (2019): 976-984.

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