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Bhowmick M, Fields GB. Synthesis of Fmoc-Gly-Ile Phosphinic Pseudodipeptide: Residue Specific Conditions for Construction of Matrix Metalloproteinase Inhibitor Building Blocks. Int J Pept Res Ther. 2012;18(4):335-339doi: 10.1007/s10989-012-9307-y.
Bhowmick, M., & Fields, G. B. (2012). Synthesis of Fmoc-Gly-Ile Phosphinic Pseudodipeptide: Residue Specific Conditions for Construction of Matrix Metalloproteinase Inhibitor Building Blocks. International journal of peptide research and therapeutics, 18(4), 335-339. https://doi.org/10.1007/s10989-012-9307-y
Bhowmick, Manishabrata, and Fields, Gregg B. "Synthesis of Fmoc-Gly-Ile Phosphinic Pseudodipeptide: Residue Specific Conditions for Construction of Matrix Metalloproteinase Inhibitor Building Blocks." International journal of peptide research and therapeutics vol. 18,4 (2012): 335-339. doi: https://doi.org/10.1007/s10989-012-9307-y
Bhowmick M, Fields GB. Synthesis of Fmoc-Gly-Ile Phosphinic Pseudodipeptide: Residue Specific Conditions for Construction of Matrix Metalloproteinase Inhibitor Building Blocks. Int J Pept Res Ther. 2012 Dec;18(4):335-339. doi: 10.1007/s10989-012-9307-y. PMID: 24496015; PMCID: PMC3564550.
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Int J Pept Res Ther. 2012 Dec;18(4):335-339. doi: 10.1007/s10989-012-9307-y.

Synthesis of Fmoc-Gly-Ile Phosphinic Pseudodipeptide: Residue Specific Conditions for Construction of Matrix Metalloproteinase Inhibitor Building Blocks.

International journal of peptide research and therapeutics

Manishabrata Bhowmick, Gregg B Fields

Affiliations

  1. Torrey Pines Institute for Molecular Studies, 11350 SW Village, Parkway, Port St. Lucie, FL 34987, USA.

PMID: 24496015 PMCID: PMC3564550 DOI: 10.1007/s10989-012-9307-y

Abstract

The efficient synthesis of an Fmoc-Gly-Ile phosphinic pseudodipeptide was desired as an eventual building block for construction of matrix metalloproteinase inhibitors. A Michael-type addition reaction of bis(tri-methylsilyl) phosphonite with the appropriate acrylate generated the pseudodipeptide bond. Additional of adamantyl (Ad) protection by our prior route (reaction of in situ generated phosphinic acid chloride with the sodium salt of adamantanol) was surprisingly inefficient. Adamantyl protection was achieved in high yield by refluxing the phosphinic acid, Ag

Keywords: Matrix metalloproteinase; Peptidomimetic; Phosphinate; Protease; Protease inhibitor; Transition state analog

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