Solid phase synthesis of fully protected peptide alcohols

Mergler, M.; Dick, Fritz; Gosteli, J.; Nyfeler, R.

doi:10.1016/s0040-4039(99)00829-1

Cited by 17 publications

(10 citation statements)

References 9 publications

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“…A synthesis method for fully protected peptide alcohols was developed using polymeric diphenyldiazomethane . This method involves the addition of a saturated solution containing an excess of Fmoc amino alcohol.…”

Section: The Redox Linker Methodsmentioning

confidence: 99%

Methods and Approaches for the Solid‐Phase Synthesis of Peptide Alcohols

Ferrer-Gago

Koh

2020

ChemPlusChem

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Many methods have been developed for attaching an alcohol functionality to a solid support. However, not all of these methods are used to obtain peptide alcohols. In this Minireview, we will discuss several of the most important methods and approaches for the synthesis of peptide alcohols and the attachment of hydroxy groups to a solid support for the synthesis of cyclic peptides. Some of the methods include the use of functionalized Wang resin and the attachment of an alcohol to an enol ether resin. We also discuss the use of the chlorotrityl resin, one of the most common linkers used to obtain peptide alcohols. In addition, we outline the recently developed resins with the Rink, Ramage and Sieber handles. The majority of these methods have been used to synthesize many important drugs, such as octreotide and the antibiotic peptaibols.

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Section: The Redox Linker Methodsmentioning

confidence: 99%

Methods and Approaches for the Solid‐Phase Synthesis of Peptide Alcohols

Ferrer-Gago

Koh

2020

ChemPlusChem

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“…However, other SPPS methods have been developed that involve reductive cleavage of a peptide ester linkage,8, 9 the use of redox‐sensitive resins,10 aminolysis of a peptide ester linkage with a β‐amino alcohol,11 or standard cleavage of a peptide alcohol ester linkage 12. Except when the chlorotrityl resin is used,13 anchoring of the hydroxy function requires derivatization of the linker or C‐terminal β‐amino alcohol with a specific handle, such as that found in tetrahydropyranyl‐based linkers,14, 15 hemisuccinate linkers,16, 17 or polymeric diphenyldiazomethane;18 alternatively, activated resins can be used 19. 20 There is still a strong need for new methodology for the preparation of peptide alcohols by the conventional 9‐fluorenylmethoxycarbonyl (Fmoc)/ t Bu SPPS strategy with commercially available resins that would enable the recovery of a nonprotected or totally protected peptide alcohol.…”

Section: Methodsmentioning

confidence: 99%

“Tolles Projekt. Das können wir nicht fördern”

2013

Nachr Chem

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Problem gelöst: C‐terminale Peptidalkohole können mit der konventionellen Festphasenpeptidsynthese (SPPS) nicht synthetisiert werden, weil sie über keine freie Carboxygruppe für das Anbinden an das Harz verfügen. Hilfe brachte das Anbinden eines β‐Aminoalkoholrests an das Harz als Startpunkt für die SPPS. Eine intramolekulare O‐N‐Acylwanderung vervollständigte die Synthese der gewünschten Peptide (siehe Schema).

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“…Tyr was anchored to Wang 2.2 and SASRIN 2.3 resins via Mitsunobu coupling [71]. Hydroxy amino acid derivatives were also immobilized as benzhydrol ethers using polymeric diphenyldiazomethane, and mild cleavage conditions with 1-2% TFA/DCM allowed synthesis of fully protected peptide alcohols [199]. Rink chloride 2.13 was converted to the Rink ether derivative 5.10 and cleaved to yield the required peptide-alcohol with 5% TFA/DCM.…”

Section: Hydroxy Groupmentioning

confidence: 99%