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Synthesis and Structure Determination of Kahalalide F1,2
Kahalalide F, the only member of the family of peptides called kahalalides, isolated from the sacoglossan mollusc Elysia rufescens and the green alga Bryopsis sp., with important bioactivity, is inExpand
Abbreviated nomenclature for cyclic and branched homo- and hetero-detic peptides.
TLDR
The aim of this contribution is to offer an unambiguous and general nomenclature system that enables researchers to represent all cyclic and branched homo- and hetero-detic peptides in a coherent manner in one-line text - as long as their as constituents can be represented in (three)-letter codes. Expand
Structure-activity relationship of kahalalide F synthetic analogues.
TLDR
The solid phase synthesis of 132 novel analogues of kahalalide F revealed that KF is highly sensitive to backbone stereotopical modification but not to side chain size modification, suggesting that this compound has a defined conformational structure. Expand
Kahalalide B. Synthesis of a natural cyclodepsipeptide
Abstract A suitable combination of soluble and polymeric protecting groups and coupling reagents has allowed the first synthesis of the natural cyclodepsipeptide of marine origin Kahalalide B to beExpand
Synthesis and structure determination of kahalalide F (1,2).
TLDR
HPLC, high-field NMR, and biological activity studies showed that the correct stereochemistry of the natural product is that proposed by Rinehart et al, whereas the stereochemistry proposed by Scheuer et al. is that of a biologically less active diastereoisomer. Expand
Synthesis of peptides containing α, β-didehydroamino acids. Scope and limitations
α, β-Didehydroamino acids, which are key components of both natural andde novo peptides, are frequently encountered in naturally occurring peptides — mostly of microbial and fungal origin and/or fromExpand
Solid-phase synthesis of the cyclic lipononadepsipeptide [N-Mst(Ser1), d-Ser4, L-Thr6, L-Asp8, L-Thr9]syringotoxin.
TLDR
An optimized solid-phase strategy for the preparation of the cyclic lipononadepsipeptide is reported, based on the use of a mild orthogonal protection scheme and the incorporation of the nonproteinogenic amino acid (Z)-Dhb into the peptide chain as the dipeptide Fmoc-Thr(tBu)-(Z)-dhb-OH. Expand
Tentoxin as a scaffold for drug discovery. Total solid-phase synthesis of tentoxin and a library of analogues.
TLDR
A solid-phase method for the synthesis of tentoxin has been developed and should be applicable to the generation of further libraries that have the tentoxin scaffold structure, as well as other structures containing N-alkylated didehydroamino acids. Expand
Solid‐Phase Synthesis of Peptides Containing α,β‐Didehydroamino Acids
α,β-Didehydroamino acids are frequently encountered in natural peptides with important biological activity. Herein, we report a mild and convenient method for the preparation of peptides containingExpand
Synthesis of peptides containing α,β-didehydroamino acids. Scope and limitations
α, β-Didehydroamino acids, which are key componentsof both natural and de novo peptides, are frequently encountered in naturally occurring peptides – mostly of microbial and fungal origin and/or fromExpand
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