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

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
ABSTRACT

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.

MATERIALS
Product Number
Brand
Product Description

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