Orthogonal Protecting Groups and Side‐Reactions in Fmoc/<i>t</i>Bu Solid‐Phase Peptide Synthesis

Carganico, Stefano; Papini, Anna Maria

doi:10.1002/9783527631803.ch9

Cited by 3 publications

(1 citation statement)

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“…We present herein the first example of microwave-assisted covalent grafting of an amino acid and various oligopeptides (up to tetrapeptides) inside MOF cavities, for the design of chiral hybrid solids. Typically, the use of microwave irradiation during the functionalization process increases the grafting yield while preventing the racemization of the peptide, a known pitfall in related strategies. , Also, proof-of-concept experiments demonstrate the asymmetric nature of the MOF-based catalysts.…”

Section: Introductionmentioning

confidence: 99%

Enantiopure Peptide-Functionalized Metal–Organic Frameworks

et al. 2015

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We present herein the first example of metal-organic frameworks postfunctionalized with peptides. Our microwave-assisted postsynthetic modification method yields enantiopure peptides anchored inside MOF cavities. Al-MIL-101-NH2, In-MIL-68-NH2, and Zr-UiO-66-NH2 were chosen as starting platforms. A single amino acid and various oligopeptides are grafted with yields up to 60% after a 30 min microwave-assisted coupling-deprotection sequence. This allows efficient preparation of a library of functional hybrid solids for molecular recognition applications such as sensing, separation, or asymmetric catalysis, as demonstrated here for the chiral aldol reaction.

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Section: Introductionmentioning

confidence: 99%

Enantiopure Peptide-Functionalized Metal–Organic Frameworks

et al. 2015

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ChemInform Abstract: Orthogonal Protecting Groups and Side‐Reactions in Fmoc/tBu Solid‐Phase Peptide Synthesis

Carganico

Papini

2012

ChemInform

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Suppression of alpha-carbon racemization in peptide synthesis based on a thiol-labile amino protecting group

Zhou,

Li,

Huang

et al. 2023

Nat Commun

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In conventional solid-phase peptide synthesis (SPPS), α-amino groups are protected with alkoxycarbonyl groups (e.g., 9-fluorenylmethoxycarbonyl [Fmoc]). However, during SPPS, inherent side reactions of the protected amino acids (e.g., α-C racemization and aspartimide formation) generate by-products that are hard to remove. Herein, we report a thiol-labile amino protecting group for SPPS, the 2,4-dinitro-6-phenyl-benzene sulfenyl (DNPBS) group, which is attached to the α-amino group via a S–N bond and can be quantitatively removed in minutes under nearly neutral conditions (1 M p-toluenethiol/pyridine). The use of DNPBS greatly suppresses the main side reactions observed during conventional SPPS. Although DNPBS SPPS is not as efficient as Fmoc SPPS, especially for synthesis of long peptides, DNPBS and Fmoc are orthogonal protecting groups; and thus DNPBS SPPS and Fmoc SPPS can be combined to synthesize peptides that are otherwise difficult to obtain.

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Orthogonal Protecting Groups and Side‐Reactions in Fmoc/tBu Solid‐Phase Peptide Synthesis

Cited by 3 publications

References 154 publications

Enantiopure Peptide-Functionalized Metal–Organic Frameworks

Enantiopure Peptide-Functionalized Metal–Organic Frameworks

ChemInform Abstract: Orthogonal Protecting Groups and Side‐Reactions in Fmoc/tBu Solid‐Phase Peptide Synthesis

Suppression of alpha-carbon racemization in peptide synthesis based on a thiol-labile amino protecting group

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