Enzyme Mediated Concise Synthesis of NH-Fmoc-S-Trityl-C^α-Methyl Cysteine

Authors

Hari Kiran Kotapati, University of Southern MississippiFollow
Daniel R. Lawrence, University of Southern Mississippi
Shelby F. Thames, University of Southern MississippiFollow
Douglas S. Masterson, University of Southern MississippiFollow

Document Type

Article

Publication Date

1-1-2016

Department

Chemistry and Biochemistry

School

Mathematics and Natural Sciences

Abstract

A concise, chiral auxiliary free, methodology for the preparation of orthogonally protected C^α-Methyl Cysteine has been developed. Curtius rearrangement of malonate halfester from PLE hydrolysis (J. Pept. Sci. 2008, 14, 1151; J. Org. Chem. 2003, 68, 5403) and simultaneous Fmoc protection using Titanium(IV) Isopropoxide yielded Fmoc protected amino ester that is then transformed into (R)-NH-Fmoc-S-Trityl-C^α-Methyl Cysteine in three steps. For the synthesis of the S enantiomer of the protected amino acid, enantiomerically enriched CO₂-t-Bu half ester derived from PLE hydrolysis was subjected to Curtius reaction followed by Fmoc protection using Titanium(IV) Isopropoxide which is then converted to (S)-NH-Fmoc-S-Trityl-C^α-Methyl Cysteine in two steps.

Publication Title

Tetrahedron Letters

Volume

57

Issue

39

First Page

4389

Last Page

4391

Recommended Citation

Kotapati, H., Lawrence, D., Thames, S. F., Masterson, D. (2016). Enzyme Mediated Concise Synthesis of NH-Fmoc-S-Trityl-C^α-Methyl Cysteine. Tetrahedron Letters, 57(39), 4389-4391.
Available at: https://aquila.usm.edu/fac_pubs/19734