Synthesis, crystal structure and Hirshfeld surface analysis of Fmoc-β-amino butyric acid and Fmoc carbamate

In the context of the development of synthetic routes that facilitate the incorporation of β-amino acids into peptide synthesis, the synthesis, crystal structure and Hirshfeld surface analysis are reported of fluorenyl­meth­oxy­carbonyl (Fmoc) protected β-amino butyric acid, namely, 3-{[(9H-fluoren-9-ylmeth­oxy)carbon­yl]amino}­butanoic acid, C19H19NO4. The importance of pH control in the reaction employing Fmoc-N3 is demonstrated with another β-amino acid analogue from which Fmoc carbamate was identified as the major product.

Publication Details

Journal
White Rose Research Online (University of Leeds, The University of Sheffield, University of York)
Published
2025-06-01
Primary Topic
Chemical Synthesis and Analysis
Type
article
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article

Synthesis, crystal structure and Hirshfeld surface analysis of Fmoc-β-amino butyric acid and Fmoc carbamate

White Rose Research Online (University of Leeds, The University of Sheffield, University of York)
Chemical Synthesis and Analysis
article

Synthesis, crystal structure and Hirshfeld surface analysis of Fmoc-β-amino butyric acid and Fmoc carbamate

article en

Abstract

In the context of the development of synthetic routes that facilitate the incorporation of β-amino acids into peptide synthesis, the synthesis, crystal structure and Hirshfeld surface analysis are reported of fluorenyl­meth­oxy­carbonyl (Fmoc) protected β-amino butyric acid, namely, 3-{[(9H-fluoren-9-ylmeth­oxy)carbon­yl]amino}­butanoic acid, C19H19NO4. The importance of pH control in the reaction employing Fmoc-N3 is demonstrated with another β-amino acid analogue from which Fmoc carbamate was identified as the major product.

White Rose Research Online (University of Leeds, The University of Sheffield, University of York)
Clean water and sanitation
Openalex Percentile: Top 38%
Chemical Synthesis and Analysis
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Synthesis, crystal structure and Hirshfeld surface analysis of Fmoc-β-amino butyric acid and Fmoc carbamate · White Rose Research Online (University of Leeds, The University of Sheffield, University of York) (2025) | TGRS Research Map | TGRS