Synthesis and NMR Studies of Cyclopeptides Containing a Sugar Amino Acid

Synthesis and NMR Studies of Cyclopeptides Containing a Sugar Amino Acid

Cyclopeptides containing Glucuronic acid methylamine (Gum) alternating with Gly, l-Ala, d-Ala, l-Phe, d-Phe, l-Lys, or d-Lys were synthesized by a combination of solid-phase synthesis and solution chemistry. A more effective pathway to synthesize the sugar amino acid Gum in higher yields and in a sh...

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Veröffentlicht in:Organic letters 2002-07, Vol.4 (15), p.2501-2504
Hauptverfasser: Stöckle, Matthias, Voll, Georg, Günther, Robert, Lohof, Elisabeth, Locardi, Elsa, Gruner, Sibylle, Kessler, Horst
Format: Artikel
Sprache:eng
Schlagworte:
Amines - chemistry
Glucuronates - chemistry
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Peptides, Cyclic - chemical synthesis
Stereoisomerism
Sugar Acids - chemistry
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container_end_page 2504
container_issue 15
container_start_page 2501
container_title Organic letters
container_volume 4
creator Stöckle, Matthias
Voll, Georg
Günther, Robert
Lohof, Elisabeth
Locardi, Elsa
Gruner, Sibylle
Kessler, Horst
description Cyclopeptides containing Glucuronic acid methylamine (Gum) alternating with Gly, l-Ala, d-Ala, l-Phe, d-Phe, l-Lys, or d-Lys were synthesized by a combination of solid-phase synthesis and solution chemistry. A more effective pathway to synthesize the sugar amino acid Gum in higher yields and in a shorter period of time was developed. Gum is employed in the benzylated and deprotected form. The cyclopeptides were characterized by NMR and the structure of one deprotected cyclic peptide solved.
doi_str_mv 10.1021/ol026126d
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source MEDLINE; American Chemical Society Journals
subjects Amines - chemistry
Glucuronates - chemistry
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Peptides, Cyclic - chemical synthesis
Stereoisomerism
Sugar Acids - chemistry
title Synthesis and NMR Studies of Cyclopeptides Containing a Sugar Amino Acid
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