Solid-Phase Preparation of a Library Based on a Phenylalanine Scaffold

Colombo, Aina; Fernàndez, Joan-Carles; Figuera, Natalia de la; Fernandez‐Forner, Dolors; Forns, Pilar; Alberício, Fernando

doi:10.1002/qsar.200420105

Cited by 9 publications

(6 citation statements)

References 15 publications

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“…Instead of synthesizing a new peptide with Ala 1 being introduced under the Boc form, we removed the Fmoc moiety and replaced it with a Boc group using the (Boc) 2 O anhydride (Scheme ). Moreover, a recent study reported that H 2 N-Phe( p I)-OH anchored to a Wang linker was not totally stable to Suzuki conditions because of the base-catalyzed hydrolysis . Thus, the reaction was attempted a second time but with a Boc protection approach at the N-terminus.…”

Section: Resultsmentioning

confidence: 99%

Effectiveness of the Suzuki−Miyaura Cross-Coupling Reaction for Solid-Phase Peptide Modification

Doan¹,

Bourgault²,

Létourneau³

et al. 2008

J. Comb. Chem.

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The Suzuki-Miyaura (SM) cross-coupling reaction has recently become one of the most efficient methods for C-C bond construction opening a wide range of opportunities in organic synthesis. This study focused on the evaluation of the use of the SM reaction to modify peptides using a solid-phase synthesis approach, an avenue that was still not investigated intensively. We used as a peptide model [Ala (1,2,3), Leu (8)]Enk linked to a polystyrene support on which it was previously assembled. The aromatic residues Tyr (4) and Phe (7) of [Ala (1,2,3), Leu (8)]Enk were respectively substituted with p-iodo-Phe, and an SM-related strategy was developed. Results indicated that the reaction conditions involving K 3PO 4 or Na 2CO 3 (base), DMF (solvent), Pd(PPh 3) 4 (catalyst), and temperatures ranging from 50 to 80 degrees C during 20 h were found as optimal. Finally applying those optimal conditions, a series of [Ala (1,2,3), Leu (8)]Enk analogs modified at Tyr (4) or Phe (7) positions was synthesized using diverse boronic acid derivatives.

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Section: Resultsmentioning

confidence: 99%

Effectiveness of the Suzuki−Miyaura Cross-Coupling Reaction for Solid-Phase Peptide Modification

Doan¹,

Bourgault²,

Létourneau³

et al. 2008

J. Comb. Chem.

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“…In this sense, cyclic peptides, either naturally occurring or synthetically constructed, and C -modified peptides have proven to be excellent molecular scaffolds for design purposes . In this field of research, phenylalanine has become an important pharmacophore in SAR studies because of the key role that plays eliciting intrinsic activity in compounds that contain this amino acid . Thus, the nonpolar nature and steric bulkiness of its side chain is responsible for crucial hydrophobic interactions in molecular recognition processes .…”

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confidence: 99%

Solid-Phase Synthesis of Phenylalanine Containing Peptides Using a Traceless Triazene Linker

et al. 2012

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The use of a triazene function to anchor phenylalanine to a polymeric support through its side chain is reported. To prove the usefulness of this strategy in solid-phase peptide synthesis, several bioactive peptides have been prepared including cyclic, C-modified, and protected peptides. The triazene linkage is formed by coupling the diazonium salt of Fmoc-Phe(pNH(2))-OAllyl to a MBHA-polystyrene resin previously functionalized with isonipecotic acid (90%). Further assembly of the peptide chain, cleavage from the resin using 2-5% TFA in DCM, and reduction of the resulting diazonium salt of the peptide with FeSO(4)·7H(2)O in DMF afforded the desired products in high purities (73-94%).

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“…The preparation of the carbamate derivatives 10 was attempted under various conditions via activation of the alcohol with Disuccinimidyl Carbonate (DSC) (entries 1 -5, Table 4) [9].…”

Section: Resultsmentioning

confidence: 99%

Solid Phase Preparation of 1,3‐Disubstituted Indazole derivatives

et al. 2008

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The immobilization and reactions of indazol-3-carboxylic acid on the solid phase is described. These reactions are of importance since many biologically active compounds contain an indazole core. Here, indazole 3-carboxylic acid was efficiently anchored onto the solid phase via a protecting group strategy. The indazolic NH was then derivatized to sulfonamides, ureas, amides, carbamates, and amines. Depending on compound class yield and purity varied but was generally high.

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Solid-Phase Preparation of a Library Based on a Phenylalanine Scaffold

Cited by 9 publications

References 15 publications

Effectiveness of the Suzuki−Miyaura Cross-Coupling Reaction for Solid-Phase Peptide Modification

Effectiveness of the Suzuki−Miyaura Cross-Coupling Reaction for Solid-Phase Peptide Modification

Solid-Phase Synthesis of Phenylalanine Containing Peptides Using a Traceless Triazene Linker

Solid Phase Preparation of 1,3‐Disubstituted Indazole derivatives

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