Synthesis of depsipeptides from <italic>L</italic>-amino acids and lactones

doi:10.1007/s11705-011-1141-9

Front Chem Sci Eng

2011, Vol. 5

Issue (4) : 409-415 https://doi.org/10.1007/s11705-011-1141-9

RESEARCH ARTICLE

Synthesis of depsipeptides from L-amino acids and lactones

Hongfei CAO¹, Yakai FENG^1,2(

), Heyun WANG¹, Li ZHANG¹, Musammir KHAN¹, Jintang GUO^1,2

1. School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, China; 2. Tianjin University-Helmholtz-Zentrum Geesthacht, Joint Laboratory for Biomaterials and Regenerative Medicine, Tianjin 300072, China; Teltow 14513, Germany

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Abstract

By using the corresponding L-amino acid sodium as initiator, ?-caprolactone-depsipeptides CL-Ala and CL-Leu were prepared by the reactions of ?-caprolactone (CL) with L-alanine and L-leucine, respectively, and p-dioxanone-depsipeptide (PDO-Leu) was prepared by the reaction of p-dioxanone (PDO) with L-leucine. Two poly(?-caprolactone) oligomers (PCL-Ala and PCL-Leu) of different molecular weights with depsipeptide unit were synthesized by controlling the feed ratio of L-amino acid sodium and CL. The presence of the depsipeptide structure in these obtained products was confirmed by ¹H NMR spectra and the molecular weight of the poly(?-caprolactone) oligomers was measured by gel permeation chromatography (GPC). These products contain a hydroxyl group and a carboxyl group in one molecule, which means they could act as bifunctional monomers for further polymerization to prepare high molecular weight polymers. By this way, the depsipeptide unit could be introduced into the polymers and the biodegradation rates of the novel polymers could be well controlled in vivo by the tailored molecular structures.

Keywords ?-caprolactone p-dioxanone L-alanine L-leucine depsipeptide

Corresponding Author(s): FENG Yakai,Email:yakaifeng@tju.edu.cn

Issue Date: 05 December 2011

Cite this article:

Hongfei CAO,Yakai FENG,Heyun WANG, et al. Synthesis of depsipeptides from L-amino acids and lactones[J]. Front Chem Sci Eng, 2011, 5(4): 409-415.

URL:

https://academic.hep.com.cn/fcse/EN/10.1007/s11705-011-1141-9
https://academic.hep.com.cn/fcse/EN/Y2011/V5/I4/409

Fig.1 Synthetic routes for the depsipeptides from lactones

Fig.2 H NMR spectrum of CL-Ala (a) and CL-Leu (b) in CDCl at 25°C

Fig.3 H NMR spectrum of PDO-Leu in DMSO- at 25°C

Tab.1 The molecular weight of the PCL-Ala and PCL-Leu

Fig.4 H NMR spectrum of PCL-Ala in CDCl at 25°C ( = 2172)

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