Figure 1: Alkyne macrocyclization. | Nature Communications

Figure 1: Alkyne macrocyclization.

From: Orthogonal ring-closing alkyne and olefin metathesis for the synthesis of small GTPase-targeting bicyclic peptides

Figure 1

(a) The linear peptide is assembled via SPPS including the incorporation of two α-methylated-α-alkynylated building blocks (1–4). The C-terminal building block is always (S)-configured, the configuration of the N-terminal building block varies between the different architectures. Complex 5 is used to perform the RCAM reaction. (i=2, 3, 6, number of amino acids between non-natural building blocks; j=3, 6; m=1, 2, 4; n=1, 2; R=side chain of a proteinogenic amino acid) (b) Fluorenylmethoxycarbonyl (Fmoc) protected non-natural amino acids incorporated into the peptide sequence (alkyne: 1–4, olefin: 6). The alkyne building blocks 1–4 are either used in the (S)- or (R)-configuration depending on the macrocycle architecture. Mo-complex (5) used for RCAM.

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