Fmoc-L-propargylglycine
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Fmoc-L-propargylglycine

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Category
Fmoc-Amino Acids
Catalog number
BAT-007455
CAS number
198561-07-8
Molecular Formula
C20H17NO4
Molecular Weight
335.35
Fmoc-L-propargylglycine
IUPAC Name
(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)pent-4-ynoic acid
Synonyms
Fmoc-L-propargyl-Gly-OH; Fmoc-L-Pra-OH; (S)-2-(Fmoc-amino)-4-pentynoic acid; Fmoc L Pra OH
Related CAS
220497-98-3 (D-isomer)
Appearance
White to off-white powder
Purity
≥ 99.5% (Chiral HPLC)
Density
1.292 g/cm3
Melting Point
175-177 °C
Boiling Point
576.7°C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C20H17NO4/c1-2-7-18(19(22)23)21-20(24)25-12-17-15-10-5-3-8-13(15)14-9-4-6-11-16(14)17/h1,3-6,8-11,17-18H,7,12H2,(H,21,24)(H,22,23)/t18-/m0/s1
InChI Key
DJGMNCKHNMRKFM-SFHVURJKSA-N
Canonical SMILES
C#CCC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
1. On-DNA-1,2,3-Triazole Formation via Click Reaction
Sarah K Scott Methods Mol Biol. 2022;2541:39-43. doi: 10.1007/978-1-0716-2545-3_6.
Copper-catalyzed azide-alkyne cycloaddition (CuAAC) provides a simple and convenient strategy to synthesize diverse 1,2,3-triazoles for drug discovery. Described herein is a protocol for the CuSO4-catalyzed cycloaddition between alkynes and DNA-appended azides.
2. A concomitant allylic azide rearrangement/intramolecular azide-alkyne cycloaddition sequence
Rakesh H Vekariya, Ruzhang Liu, Jeffrey Aubé Org Lett. 2014 Apr 4;16(7):1844-7. doi: 10.1021/ol500011f. Epub 2014 Mar 17.
An intramolecular Huisgen cycloaddition of an interconverting set of isomeric allylic azides with alkynes affords substituted triazoles in high yield. The stereoisomeric vinyl-substituted triazoloxazines formed depend on the rate of cycloaddition of the different allylic azide precursors when the reaction is carried out under thermal conditions. In contrast, dimerized macrocyclic products were obtained when the reaction was done using copper(I)-catalyzed conditions, demonstrating the ability to control the reaction products through changing conditions.
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