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A facile approach for the synthesis of pseudo-peptides incorporating a (2S, 3R)-2-amino-cyclopropane carboxylic acid residue

โœ Scribed by David E. Hibbs; Michael B. Hursthouse; Iwan G. Jones; Wyn Jones; K.M.Abdul Malik; Michael North

Book ID
104208228
Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
452 KB
Volume
53
Category
Article
ISSN
0040-4020

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โœฆ Synopsis

The synthesis of a pseudo-tripeptide 9 and a pseudo-pontapoptide 1 incorporating the conformationally constrained 13-amino acid (2S,3R)-2-amino cyclopropane earbox'ylic acid is reported. The key steps of the ~'nthesis are the desynmletrisation of cyclopropane 1,2-dicarbox'ylic anhydride using (S)-proline t-butyl ester followed by a Curtius rearrangement. Subsequent trappmg of the isocyanate with (S)-proline t-butyl ester or HN-(S)-Pro-(S)-Phe-(S)-Phe-OMe gave the desired pseudo-peptides. The stereochemistry of the desymmetrisation reaction was determined by X-ray c~'stallography of the amido-acid

๐Ÿ“œ SIMILAR VOLUMES

ChemInform Abstract: A Facile Approach f
ChemInform Abstract: A Facile Approach for the Synthesis of Pseudo-Peptides Incorporating a (2S,3R)-2-Amino-cyclopropane Carboxylic Acid Residue.
โœ D. E. HIBBS; M. B. HURSTHOUSE; I. G. JONES; W. JONES; K. M. A. MALIK; M. NORTH ๐Ÿ“‚ Article ๐Ÿ“… 2010 ๐Ÿ› John Wiley and Sons โš– 34 KB ๐Ÿ‘ 2 views

A Facile Approach for the Synthesis of Pseudo-Peptides Incorporating a (2S,3R)-2-Amino-cyclopropane Carboxylic Acid Residue. -The new approach to the synthesis of the title compounds is based on the desymmetrization of meso-anhydride (I) followed by a Curtius rearrangement to obtain key building bl