Synthesis and NMR studies of cyclopeptides containing a sugar amino Acid.
[structure: see text] 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.
Institut für Organische Chemie und Biochemie, Technische Universität München, Lichtenbergstr. 4, D-85747 Garching, Germany.
Matthias
M
Stöckle
Georg
G
Voll
Robert
R
Günther
Elisabeth
E
Lohof
Elsa
E
Locardi
Sibylle
S
Gruner
Horst
H
Kessler
D000588:Amines / Q000737:chemistry*; D005965:Glucuronates / Q000737:chemistry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010456:Peptides, Cyclic / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013400:Sugar Acids / Q000737:chemistry*
D000588:Amines; D005965:Glucuronates; D010456:Peptides, Cyclic; D013400:Sugar Acids