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Diversity-oriented synthesis of azapeptides with basic amino acid residues: aza-lysine, aza-ornithine, and aza-arginine.

Organic letters (2014-06-25)
Mariam Traoré, Ngoc-Duc Doan, William D Lubell
RESUMEN

Aza-peptides with basic amino acid residues (lysine, ornithine, arginine) and derivatives were synthesized by an effective approach featuring alkylation of a hydrazone-protected aza-glycine residue with α-bromo ω-chloro propane and butane to provide the corresponding alkyl chloride side chains. Displacement of the chloride with azide and various amines gave entry to azaOrn, azaLys, and azaArg containing peptides as demonstrated by the solution and solid-phase syntheses of 29 examples, including an aza-library of Growth Hormone Releasing Peptide-6 analogs.

MATERIALES
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Sigma-Aldrich
L-arginina, from non-animal source, meets EP, USP testing specifications, suitable for cell culture, 98.5-101.0%
Sigma-Aldrich
L-Lisina, ≥98% (TLC)
Sigma-Aldrich
L-Lysine monohydrochloride, from non-animal source, meets EP, JP, USP testing specifications, suitable for cell culture, 98.5-101.0%
Sigma-Aldrich
L-Ornithine monohydrochloride, ≥99%
Sigma-Aldrich
L-Lisina, crystallized, ≥98.0% (NT)
SAFC
L-arginina
Sigma-Aldrich
L-arginina, 99%, FCC, FG
Sigma-Aldrich
L-Ornithine monohydrochloride, BioReagent, suitable for cell culture, ≥99%
Sigma-Aldrich
L-arginina, reagent grade, ≥98%
Sigma-Aldrich
L-Ornithine hydrochloride, 99%
Sigma-Aldrich
L-Lysine monohydrochloride, reagent grade, ≥98% (HPLC)
Sigma-Aldrich
L-arginina, BioUltra, ≥99.5% (NT)
Sigma-Aldrich
L-Ornithine monohydrochloride, BioXtra, ≥99%
Sigma-Aldrich
L-Lysine acetate salt, ≥98% (HPLC)
Sigma-Aldrich
D-Ornithine monohydrochloride, ~98%
Sigma-Aldrich
L-Ornithine dihydrochloride, ≥99.0% (AT)
L-arginina, European Pharmacopoeia (EP) Reference Standard
Sigma-Aldrich
DL-Ornithine monohydrochloride, ≥99.0% (AT)
Supelco
L-Lisina, analytical standard
Supelco
L-arginina, Pharmaceutical Secondary Standard; Certified Reference Material
Supelco
L-Lysine monohydrochloride, Pharmaceutical Secondary Standard; Certified Reference Material
Lysine hydrochloride, European Pharmacopoeia (EP) Reference Standard
Sigma-Aldrich
L-Lysine monohydrochloride, BioUltra, ≥99.5% (AT)
Sigma-Aldrich
[D-Trp7, Ala8, D-Phe10]-α-Melanocyte Stimulating Hormone Amide Fragment 6-11, ≥97% (HPLC)
Supelco
L-Lysine monohydrochloride, certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland
Supelco
L-Lysine Acetate, Pharmaceutical Secondary Standard; Certified Reference Material
Sigma-Aldrich
L-Lysine monohydrochloride, SAJ special grade, ≥99.0%
Lysine acetate, European Pharmacopoeia (EP) Reference Standard