A General Preparation of Protected Phosphoamino Acids

Petrillo, Daniel E.; Mowrey, Dale R.; Allwein, Shawn P.; Bakale, Roger P.

doi:10.1021/ol203332j

Cited by 12 publications

(15 citation statements)

References 20 publications

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“…This method has largely been superseded by the building block approach, owing to its greater convenience . For introduction of phosphotyrosine, free phosphate, phosphodiester and triester, phosphoamidate‐based building blocks are available (Table ).…”

Section: Introductionmentioning

confidence: 99%

Advances in Fmoc solid‐phase peptide synthesis

Behrendt

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2016

Journal of Peptide Science

562

426

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Today, Fmoc SPPS is the method of choice for peptide synthesis. Very‐high‐quality Fmoc building blocks are available at low cost because of the economies of scale arising from current multiton production of therapeutic peptides by Fmoc SPPS. Many modified derivatives are commercially available as Fmoc building blocks, making synthetic access to a broad range of peptide derivatives straightforward. The number of synthetic peptides entering clinical trials has grown continuously over the last decade, and recent advances in the Fmoc SPPS technology are a response to the growing demand from medicinal chemistry and pharmacology. Improvements are being continually reported for peptide quality, synthesis time and novel synthetic targets. Topical peptide research has contributed to a continuous improvement and expansion of Fmoc SPPS applications. Copyright © 2015 European Peptide Society and John Wiley & Sons, Ltd.

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Section: Introductionmentioning

confidence: 99%

Advances in Fmoc solid‐phase peptide synthesis

Behrendt

White

Offer

2016

Journal of Peptide Science

562

426

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“…Fmoc- allo -pThr(Bn)-OH (for P15 ) and Cbz-pThr(Bn)-OH (for P21 ) were synthesized according to literature precedent. 54…”

Section: Methodsmentioning

confidence: 99%

Divergent Stereoselectivity in Phosphothreonine (pThr)-Catalyzed Reductive Aminations of 3-Amidocyclohexanones

et al. 2018

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Phosphothreonine (pThr)-embedded peptide catalysts are found to mediate the reductive amination of 3-amidocyclohexanones with divergent selectivity. The choice of peptide sequence can be used to alter the diastereoselectivity to favor either the cis-product or trans-product, which are obtained in up to 93:7 er. NMR studies and DFT calculations are reported and indicate that both pathways rely on secondary interactions between substrate and catalyst to achieve selectivity. Furthermore, catalysts appear to accomplish a parallel kinetic resolution of the substrates. The facility for phosphopeptides to tune reactivity and access multiple products in reductive aminations may translate to the diversification of complex substrates, such as natural products, at numerous reactive sites.

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“…The choice of the naphthyl rather than phenyl as the aryl motif was critical Scheme 3 Novel one-pot synthesis of Fmoc-Tyr(PO(OBzl)OH)-OH. 67…”

Section: Rsc Medicinal Chemistry Reviewmentioning

confidence: 99%