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Synfacts 2022; 18(03): 0339
DOI: 10.1055/s-0041-1737821
Peptide Chemistry

A Silyl Carbamate Linker for Solid-State Peptide Synthesis in the Reverse Direction

Contributor(s):
Hisashi Yamamoto
,
Isai Ramakrishna
Lipshutz BH, *, Shin Y.-J. University of California, Santa Barbara, USA
A New Silyl Linker for Reverse-Direction Solid-Phase Peptide Synthesis.

Tetrahedron Lett. 2001;
42: 5629-5633
DOI: 10.1016/S0040-4039(01)01093-0.
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Key words

silyl carbamates - linking group - solid phase synthesis - polypeptides

Significance

Silicon-containing solid supports play an inherent role in solid-state peptide synthesis. Consequently, chemists are in search of elegant and practical supports for peptide synthesis. In 2001, Lipshutz and Shin developed a novel and easily accessible silyl carbamate linker for peptide synthesis.


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Comment

Polystyrene-bound silyl carbamates of amino acid esters were synthesized by treatment of amino acid esters with gaseous CO2 in dichloromethane, with subsequent trapping of the polymer-bound silyl chloride. The resulting polystyrene-bound silyl carbamates of amino acid esters can be used in solid-state syntheses of polypeptides, building from the carboxy terminus.


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Publication History

Article published online:
16 February 2022

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