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Design of peptides with α, β-dehydro-residues: synthesis and crystal structure of a tripeptide N-benzyloxycarbonyl-ΔVal-ΔPhe-l-Ala-OCH3

✍ Scribed by Vijay Kumar Goel; Sharmistha Dey; Tej P. Singh

Publisher
Elsevier Science
Year
2005
Tongue
English
Weight
183 KB
Volume
738
Category
Article
ISSN
0022-2860

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Highly specific peptide structures can be designed by inserting dehydro residues into peptide sequences. The peptide N-Boc-L-Phe-dehydro-Phe-L-Val-L-Phe-dehydro-Phe-~-V~-OCH~, synthesized by conventional procedures, crystallizes from methanol-water mixtures at 4°C in the tetragonal space group P43 w

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The dehydro-residue containing peptides N-Ac-dehydro-Phe-L-Leu-OCH3 ( I ) and N-Acdehydro-Phe-NorVal-OCH, (11) were synthesized by the usual workup procedures. The peptides crystallize from their solutions in methanol in space group P6,: ( I ) a = b = 12.528(2) A, c = 21.653(5) A; (11) a = b = 12.53

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Design of peptides: Synthesis, crystal structure, molecular conformation, and conformational calculations of N-Boc-L-Phe-Dehydro-Ala-OCH3
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## Abstract It is noteworthy that the dehydro‐Ala residue adopts an extended conformation that is different than those observed in dehydro‐Phe, dehydro‐Leu, and dehydro‐Abu. The peptide N‐Boc‐L ‐Phe‐dehydro‐Ala‐OCH~3~ (C~18~H~24~N~2~O~5~) was synthesized by the usual workup procedure and finally by