Towards peptide isostere libraries: aqueous aldol reactions on hydrophilic solid supports

Graven, Anette; Grötli, Morten; Meldal, Morten

doi:10.1039/a909246c

Cited by 25 publications

(16 citation statements)

References 40 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The emergence of water‐compatible Lewis acids has definitely broken down the wall of traditional prejudice that water is a detrimental contaminant in organic synthesis, and has also offered industrially beneficial methodologies that facilitate recovery and reuse of these catalysts. As for heterogeneous catalysis, polar polyoxyethylene‐polyoxypropylene (POE‐POP) resin, derivatized with a 4‐hydroxymethylphenoxy linker, was employed as a solid support for Ln(OTf) 3 ‐catalyzed Mukaiyama‐type solid‐phase aldol reactions 49. The utilization of an aqueous medium was crucial for the acquisition of sufficient reactivities and high yields were attained for an N‐terminal peptide aldehyde substrate 22 (Scheme ).…”

Section: Lewis Acid Catalysis In Aqueous or Organic Solventsmentioning

confidence: 99%

A Photocleavable Auxiliary for Extended Native Chemical Ligation

Nadler

Hansen

et al. 2015

Eur J Org Chem

View full text Add to dashboard Cite

To extend the scope of native chemical ligations beyond X‐Cys connections, auxiliaries that contain thiol moieties were developed to mimic the function of the Cys residue in the ligation reaction/capture step. Auxiliaries known so far feature complicated attachment protocols and generally need harsh conditions for their cleavage. Herein, we present the development of a new photoremovable ligation auxiliary, which is easily synthesized and attached to peptides that contain a variety of N‐terminal amino acids by a reductive amination reaction. Ligations at Gly‐Gly and Ala‐Gly junctions were carried out with high conversion, and the auxiliary can be cleaved from the final product by using a mild photolysis protocol. This methodological advancement is an important step forward in peptide ligation chemistry.

show abstract

Section: Lewis Acid Catalysis In Aqueous or Organic Solventsmentioning

confidence: 99%

A Photocleavable Auxiliary for Extended Native Chemical Ligation

Nadler

Hansen

et al. 2015

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

“…As for heterogeneous catalysis, polar polyoxyethylene-polyoxypropylene (POE-POP) resin, derivatized with a 4-hydroxymethylphenoxy linker, was employed as a solid support for Ln(OTf) 3 -catalyzed Mukaiyama-type solid-phase aldol reactions. 49 The utilization of an aqueous medium was crucial for the acquisition of sufficient reactivities and high yields were attained for an N-terminal peptide aldehyde substrate 22 (Scheme 9 ).…”

Section: Lewis Acid Catalysis In Aqueous or Organic Solventsmentioning

confidence: 99%

Mukaiyama Aldol Reactions in Aqueous Media

Kitanosono

Kobayashi

2013

Adv Synth Catal

View full text Add to dashboard Cite

Mukaiyama aldol reactions in aqueous media have been surveyed. While the original Mukaiyama aldol reactions entailed stoichiometric use of Lewis acids in organic solvents under strictly anhydrous conditions, Mukaiyama aldol reactions in aqueous media are not only suitable for green sustainable chemistry but are found to produce singular phenomena. These findings led to the discovery of a series of water-compatible Lewis acids such as lanthanide triflates in 1991. Our understanding on these beneficial effects in the presence of water will be deepened through the brilliant examples collected in this review.1 Introduction2 Rate Enhancement by Water in the Mukaiyama Aldol Reaction3 Lewis Acid Catalysis in Aqueous or Organic Solvents3.1 Water-Compatible Lewis Acids4 Lewis-Base Catalysis in Aqueous or Organic Solvents5 The Mukaiyama Aldol Reactions in 100% Water6 Asymmetric Catalysts in Aqueous Media and Water7 Conclusions and Perspective

show abstract

“…8 Meldal has exploited the stability of ytterbium(III) triflate under aqueous conditions in his application of the catalyst in an aldol condensation of a peptide aldehyde immobilised on a hydrophilic support. 9 The product 9 was obtained in good yield after cleavage from the support (Scheme 7). Wang has used ytterbium(III) triflate to mediate the electrophilic cyclisation of a glyoxalate-derived, unsaturated imine 10.…”

Section: Lanthanide(iii) Reagentsmentioning

confidence: 99%

Lanthanide reagents in solid phase synthesis

Sloan

Procter

2006

Chem. Soc. Rev.

View full text Add to dashboard Cite

From solid-supported ytterbium(III) catalysts to linkers cleaved by electron transfer from samarium(II) species, lanthanide reagents are beginning to find widespread application in solid phase organic synthesis. This tutorial review introduces the use of lanthanide(III) Lewis acids and lanthanide(IV) oxidants in solid phase chemistry before concentrating on the growing use of lanthanide(II) reagents in the area.

show abstract

Towards peptide isostere libraries: aqueous aldol reactions on hydrophilic solid supports

Cited by 25 publications

References 40 publications

A Photocleavable Auxiliary for Extended Native Chemical Ligation

A Photocleavable Auxiliary for Extended Native Chemical Ligation

Mukaiyama Aldol Reactions in Aqueous Media

Lanthanide reagents in solid phase synthesis

Contact Info

Product

Resources

About