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N-(p-Ethynylbenzoyl) derivatives of amino acid and dipeptide methyl esters - Synthesis and structural study
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DOI：10.1016/j.molstruc.2011.08.034.png)
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Abstract
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A series of N-(p-ethynylbenzoyl) derivatives (1-4) of the amino acids glycine and L-alanine as well as the dipeptides glycylglycine and L-alanylglycine has been synthesized via a two-step reaction sequence including the reaction of an appropriate N-(p-bromobenzoyl) precursor with trimethylsilylacetylene followed by deprotection of the trimethylsilyl protecting group, respectively. X-ray crystal structures of the amino acid and dipeptide methyl esters 1-4 are reported. The amide and peptide bonds within each molecular structure are planar and adopt the trans-configuration. The packing structures are governed by N-H center dot center dot center dot O interactions leading to the formation of characteristic strand motifs. Further stabilization results from weaker C-H center dot center dot center dot O and C-H center dot center dot center dot pi contacts. (C) 2011 Elsevier B.V. All rights reserved.
Keywords:
N-(p-ethynylbenzoyl) amino acid
N-(p-ethynylbenzoyl) peptide
X-ray crystal structure
Hydrogen bonding
Strand packing motif
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