Resolution of protected silaproline for a gram scale preparation

C. Martin; N. Vanthuyne; H. Miramon; J. Martinez; F. Cavelier

doi:10.1007/s00726-011-1112-y

Amino Acids

August 2012, Volume 43, Issue 2, pp 649–655

Resolution of protected silaproline for a gram scale preparation

Authors
Authors and affiliations

C. Martin
N. Vanthuyne
H. Miramon
J. Martinez
F. CavelierEmail author

Original Article

First Online:: 15 October 2011

Received:: 13 May 2011
Accepted:: 26 September 2011

DOI: 10.1007/s00726-011-1112-y

Cite this article as:: Martin, C., Vanthuyne, N., Miramon, H. et al. Amino Acids (2012) 43: 649. doi:10.1007/s00726-011-1112-y

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Abstract

Silaproline is an analogue of proline, which exhibits similar conformational properties. Moreover, the presence of dimethylsilyl group confers to silaproline a higher lipophilicity as well as an improved resistance to biodegradation. This report describes the comparison of two routes to obtain Fmoc-(l) Sip-OH on the gram scale using chiral HPLC resolution.

Keywords

Silaproline Chiral HPLC resolution Absolute configuration Enantiomers

References

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Authors and Affiliations

C. Martin
- 1
N. Vanthuyne
- 2
H. Miramon
- 1
J. Martinez
- 1
F. Cavelier
- 1
Email author

1.IBMM, UMR-CNRS-5247Universités Montpellier I and IIMontpellierFrance
2.UPCAM, ISm2, UMR-6263Université Paul CézanneMarseilleFrance

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Resolution of protected silaproline for a gram scale preparation

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