Enantioselective recognition of histidine and lysine esters by porphyrin chiral clefts and detection of amino acid conformations in the bound state

Maxwell J. Crossley; Lindsey G. MacKay; Andrew C. Try

doi:10.1039/C39950001925

Enantioselective recognition of histidine and lysine esters by porphyrin chiral clefts and detection of amino acid conformations in the bound state

Maxwell J. Crossley^*, Lindsey G. MacKay, Andrew C. Try

^*Corresponding author for this work

Macquarie University BioFocus Research Centre

Research output: Contribution to journal › Article › peer-review

151 Citations (Scopus)

Abstract

Resolution of the bisporphyrin Tröger's base analogue 1 affords homochiral clefts that tightly bind histidine esters in 80-86% e.e. and lysine benzyl ester in 48% e.e.; the histidine esters are bound in fixed conformations that can be readily detected by ¹H NMR spectroscopy as a result of the large dispersion of proton resonances by the ring currents of the two porphyrins.

Original language	English
Pages (from-to)	1925-1927
Number of pages	3
Journal	Journal of the Chemical Society, Chemical Communications
Issue number	18
DOIs	https://doi.org/10.1039/C39950001925
Publication status	Published - 1995

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title = "Enantioselective recognition of histidine and lysine esters by porphyrin chiral clefts and detection of amino acid conformations in the bound state",

abstract = "Resolution of the bisporphyrin Tr{\"o}ger's base analogue 1 affords homochiral clefts that tightly bind histidine esters in 80-86% e.e. and lysine benzyl ester in 48% e.e.; the histidine esters are bound in fixed conformations that can be readily detected by 1H NMR spectroscopy as a result of the large dispersion of proton resonances by the ring currents of the two porphyrins.",

author = "Crossley, {Maxwell J.} and MacKay, {Lindsey G.} and Try, {Andrew C.}",

year = "1995",

doi = "10.1039/C39950001925",

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T1 - Enantioselective recognition of histidine and lysine esters by porphyrin chiral clefts and detection of amino acid conformations in the bound state

AU - Crossley, Maxwell J.

AU - MacKay, Lindsey G.

AU - Try, Andrew C.

PY - 1995

Y1 - 1995

N2 - Resolution of the bisporphyrin Tröger's base analogue 1 affords homochiral clefts that tightly bind histidine esters in 80-86% e.e. and lysine benzyl ester in 48% e.e.; the histidine esters are bound in fixed conformations that can be readily detected by 1H NMR spectroscopy as a result of the large dispersion of proton resonances by the ring currents of the two porphyrins.

AB - Resolution of the bisporphyrin Tröger's base analogue 1 affords homochiral clefts that tightly bind histidine esters in 80-86% e.e. and lysine benzyl ester in 48% e.e.; the histidine esters are bound in fixed conformations that can be readily detected by 1H NMR spectroscopy as a result of the large dispersion of proton resonances by the ring currents of the two porphyrins.

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U2 - 10.1039/C39950001925

DO - 10.1039/C39950001925

M3 - Article

AN - SCOPUS:37049073344

SN - 0022-4936

SP - 1925

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JO - Journal of the Chemical Society, Chemical Communications

JF - Journal of the Chemical Society, Chemical Communications

IS - 18

ER -

Enantioselective recognition of histidine and lysine esters by porphyrin chiral clefts and detection of amino acid conformations in the bound state

Abstract

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