Photolithographic synthesis of cyclic peptide arrays using a differential deprotection strategy

Li, Shuwei; Marthandan, Nishanth; Bowerman, Dawn; Garner, Harold R.; Kodadek, Thomas

doi:10.1039/b415578e

Cited by 51 publications

(24 citation statements)

References 14 publications

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“…The resulting solutions then are spotted robotically onto a chemically modified glass slide such that the library-derived molecule is attached covalently to the surface. Alternatively, methods exist for the synthesis of certain classes of compounds in situ on the array surface (6)(7)(8)(9)(10).…”

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confidence: 99%

Protein “fingerprinting” in complex mixtures with peptoid microarrays

Reddy

Kodadek

2005

Proc. Natl. Acad. Sci. U.S.A.

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We report here that microarrays comprised of several thousand peptoids (oligo-N-substituted glycines) are useful tools for the identification of proteins via a ''fingerprinting'' approach. By using maltose-binding protein, glutathione S-transferase, and ubiquitin, a specific and highly reproducible pattern of binding was observed when fluorescently labeled protein was hybridized to the array. A similar pattern was obtained when binding of an unlabeled protein to the array was visualized by secondary hybridization of a labeled antibody against that protein, showing that native proteins can be identified without the requirement for prior chemical labeling. This work suggests that small-molecule microarrays might be used for more complex fingerprinting assays of potential diagnostic value.profiling ͉ proteomics ͉ small molecule microarrays

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confidence: 99%

Protein “fingerprinting” in complex mixtures with peptoid microarrays

Reddy

Kodadek

2005

Proc. Natl. Acad. Sci. U.S.A.

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“…In 2005, Li et al reported a new chemical procedure for the in situ addition of photo-cleavable protection groups to a growing peptide chain [20].…”

Section: One-coupling-cycle-per-monomer Methodsmentioning

confidence: 99%

Printing Peptide Arrays with a Complementary Metal Oxide Semiconductor Chip

Loeffler

Cheng²,

Muenster

et al. 2013

Fundamentals and Application of New Bioproduction Systems

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: In this chapter, we discuss the state-of-the-art peptide array technologies, comparing the spot technique, lithographical methods, and microelectronic chip-based approaches. Based on this analysis, we describe a novel peptide array synthesis method with a microelectronic chip printer. By means of a complementary metal oxide semiconductor chip, charged bioparticles can be patterned on its surface. The bioparticles serve as vehicles to transfer molecule monomers to specific synthesis spots. Our chip offers 16,384 pixel electrodes on its surface with a spot-to-spot pitch of 100 μm. By switching the voltage of each pixel between 0 and 100 V separately, it is possible to generate arbitrary particle patterns for combinatorial molecule synthesis. Afterwards, the patterned chip surface serves as a printing head to transfer the particle pattern from its surface to a synthesis substrate. We conducted a series of proof-of-principle experiments to synthesize high-density peptide arrays. Our solid phase synthesis approach is based on the 9-fluorenylmethoxycarbonyl protection group strategy. After melting the particles, embedded monomers diffuse to the surface and participate in the coupling reaction to the surface. The method demonstrated herein can be easily extended to the synthesis of more complicated artificial molecules by using bioparticles with artificial molecular building blocks. The possibility of synthesizing artificial peptides was also shown in an experiment in which we patterned biotin particles in a high-density array format. These results open the road to the development of peptide-based functional modules for diverse applications in biotechnology.

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“…Using the DLP technique and a single photolabile reagent (MeNPoc-protected glycolic acid) a peptoid array was synthesized [21]. Shortly after, a strategy for the synthesis of spatially addressable arrays of cyclic peptides was also reported [22]. These experiments expanded the scope of light-directed synthesis of microarrays beyond specialized environments.…”

Section: Light-directed Synthesismentioning

confidence: 97%

Probing Biology with Small Molecule Microarrays (SMM)

Winssinger

Pianowski

Debaene

2007

Topics in Current Chemistry

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In the continuous drive to increase screening throughput and reduce sample requirement, microarray-based technologies have risen to the occasion. In the past 7 years, a number of new methodologies have been developed for preparing small molecule microarrays from combinatorial and natural product libraries with the goal of identifying new interactions or enzymatic activities. Recent advances and applications of small molecule microarrays are reviewed

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Photolithographic synthesis of cyclic peptide arrays using a differential deprotection strategy

Abstract: We report here a strategy for the photolithographic synthesis of diverse, spatially addressable arrays of cyclic peptides which employs a differential deprotection strategy for the combinatorial addition of side chains to a pre-fabricated cyclic core.

Cited by 51 publications

References 14 publications

Protein “fingerprinting” in complex mixtures with peptoid microarrays

Protein “fingerprinting” in complex mixtures with peptoid microarrays

Printing Peptide Arrays with a Complementary Metal Oxide Semiconductor Chip

Probing Biology with Small Molecule Microarrays (SMM)

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