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Solid-phase synthesis of C-terminal azapeptides.

Journal of peptide science : an official publication of the European Peptide Society (2014-11-18)
Ngoc-Duc Doan, Jinqiang Zhang, Mariam Traoré, Winnie Kamdem, William D Lubell
ABSTRACT

The solid-phase synthesis of azapeptides possessing a C-terminal aza-residue has been accomplished by a protocol featuring regioselective alkylation of benzhydrylidene-aza-glycinamide and illustrated by the syntheses of [aza-Lys(6)] growth-hormone-releasing peptide-6 analogs.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
N,N-Diisopropylethylamine, purified by redistillation, 99.5%
Sigma-Aldrich
Benzophenone hydrazone, 96%
Sigma-Aldrich
N,N′-Disuccinimidyl carbonate, ≥95%
Sigma-Aldrich
Fmoc-D-Phe-OH, ≥98.0%
Sigma-Aldrich
Boc-His(Trt)-OH, ≥98.0% (TLC)
Sigma-Aldrich
N,N-Diisopropylethylamine, ReagentPlus®, ≥99%
Sigma-Aldrich
Diethylamine, puriss. p.a., ≥99.5% (GC)
Sigma-Aldrich
Fmoc-D-Trp(Boc)-OH, ≥95.0% (HPLC)
Sigma-Aldrich
Diethylamine, purified by redistillation, 99.5%
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Hydroxylamine hydrochloride, 99.999% trace metals basis
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Pyridine, anhydrous, 99.8%
Sigma-Aldrich
4-Methylbenzyl bromide, 97%
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1-Bromo-4-chlorobutane, 99%
Sigma-Aldrich
Fmoc-Ala-OH, 95%
Sigma-Aldrich
Hydroxylamine hydrochloride, 99.995% trace metals basis
Sigma-Aldrich
Diethylamine, ≥99.5%
Sigma-Aldrich
Pyridine, ≥99%