Chen, D., Mirski, M. A., Chen, S., Bryden, W. A., McLoughlin, M., Kiser, K. M., Caton, E. R., Haddaway, C. R., Cetta, M. S., & Pan, Y. PNAS nexus (2024), 3(9).
PEG36-Nle(O-Bzl)-Met(O)2-Oic-Abu-ACC was designed in house and synthesized by CPC Scientific Inc (San Jose, CA, Fig. S1). Amino-PEG36-acid (CAS: 196936-04-6) and 2-(7-amino-2-oxochromen-4-yl)acetamide (CAS:296236-23-2) were used for the synthesis. The synthesized sensor was resuspended in high-performance liquid chromatography (HPLC)-grade water with a concentration of 200 µM.
The synthesis of the linear RP-182 analog, bicyclo[6.1.0]non-4-yn-9-ylmethyloxycarbonyl-PEG2-Lys-Phe-Arg-Lys-Ala-Phe-Lys-Arg-Phe-Phe-Lys(azido-PEG)-NH2, was achieved using standard solid-phase peptide synthesis (SPPS) protocols. After cleaving the linear peptide from the resin, macrocyclization was performed in the liquid phase through a strain-promoted click reaction. BCN introduces extra ring strain due to its fused cyclopropane structure. The combined effect of ring strain, the selection of BCN, and copper catalysis significantly increases the macrocyclization efficiency of longer peptides like RP-182.
Singh, S.S., Calvo, R., Kumari, A., Sable, R.V., Fang, Y., Tao, D., Hu, X., Castle, S.G., Nahar, S., Li, D. and Major, E. Molecular Cancer Therapeutics (2024).
- CPC Scientific Inc., 160E Tasman Dr., Suite 200, San Jose, CA 95134
[..] assembling the peptide on the Rink Amide resin and attaching the PEG azide moiety to the N-terminal Lys, the Dde group was removed as previously shown and coupled to the Fmoc-PEG2-acid. Removal of the Fmoc followed by simultaneously click/coupling to bicyclo[6.1.0]non-4-yn-9-ylmethyl (2,5-dioxopyrrolidin-1-yl) carbonate gave 1c which was deprotected and cleaved from the resin to give 1c.
Bekdemir, Ahmet, Eden EL Tanner, Jesse Kirkpatrick, Ava P. Soleimany, Samir Mitragotri, and Sangeeta N. Bhatia Advanced Healthcare Materials (2022): 2102685.
Peptides [TDN-qFAM, C-(PEG)2-K(CPQ2)-GGGSRPfGG-5FAM] were obtained from Tufts University Peptide Core Facility or CPC Scientific, Inc (USA)
Soleimany, Ava P., [..] Sangeeta N. Bhatia. Cancer Research 81, no. 1 (2021): 213-224.
All peptides were synthesized by CPC Scientific (Sunnyvale, CA) and reconstituted in dimethylformamide (DMF) unless otherwise specified. Sequences are provided in Supplementary Table S1.
Ramasubramanian, Anusuya, Riya Muckom, Caroline Sugnaux, Christina Fuentes, Barbara L. Ekerdt, Douglas S. Clark, Kevin E. Healy, and David V. Schaffer. ACS Biomaterials Science & Engineering 7, no. 4 (2021): 1344-1360.
A cyclic 11-MUA adhesion peptide (CPC Scientific Inc., Sunnyvale, CA) was also synthesized via standard Fmoc chemistry and cyclized via a lactam bond between Asp(1) and Lys(9) to form (11-MUA)-GG-PEG 2 -cyclo(DMGDGRPRK)-NH 2 or 11-MUA-cyclic (7C-1).
Paul S. Marinec, Kyle E. Landgraf, Maruti Uppalapati, Gang Chen, Daniel Xie,‡ Qiyang Jiang, Yanlong Zhao, Annalise Petriello, Kurt Deshayes, Stephen B. H. Kent, Dana Ault-Riche*, and Sachdev S. Sidhu* ACS Chem. Biol. 2021, 16, 3, 548–556.
- Chinese Peptide Company, Hangzhou Economic and Technical Development Zone, China, 310018.
"The D-VEGF-A polypeptide chain (COOH acid, residues 8-109 (1)) was chemically synthesized using solid phase peptide synthesis (SPPS) and native chemical ligation, and folded to form the protein covalent homodimer, using methods adapted from our previous work [..]"
Chan, Leslie W., Melodi N. Anahtar, Ta-Hsuan Ong, Kelsey E. Hern, Roderick R. Kunz, and Sangeeta N. Bhatia. Nature Nanotechnology (2020): 1-9.
HFA-modifed peptides were synthesized by CPC Scientifc (>95% purity). Briefy, the peptide substrate, Ac-CKKK(Cy5)-PEG4-Nle(O-Bzl)-Met(O)2-Oic-Abu-OH, was synthesized on Fmoc-Abu-CTC resin via standard Fmoc solid phase peptide synthesis.
Hao, Liangliang, Renee T. Zhao, Chayanon Ngambenjawong, Heather E. Fleming, and Sangeeta Bhatia. bioRxiv (2020).
All peptides were chemically synthesized by CPC Scientific, Inc. [..] K(N3)-ANP-GPVPLSLVMGGC [..] 5FAM-GGf-Pip-KSGGGK(CPQ2)-PEG2-GC
Buss, Colin G., and Sangeeta N. Bhatia. Proceedings of the National Academy of Sciences (2020).
Tandem Peptides. Tandem peptides were purchased from CPC Scientific. Sequences are: mTP-TAMRA-LyP1 (Myr-GWTLNSAGYLLGKINLKALA-ALAKKILGGGGK(5TAMRA)-CGNKRTRGC (C-C bridge)); [..] PEGylated formulations of these peptides were synthesized as previously described (49). The sequences are: [..] mTP-PEG-ARAL (Myr-GWTLNSAGYLLGKINLKALA-ALAKKILC-PEG5K-GGGARALPSQRSR).
