{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,9]],"date-time":"2025-11-09T07:31:36Z","timestamp":1762673496675},"reference-count":38,"publisher":"American Chemical Society (ACS)","issue":"15","content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J. Med. 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For\u00e7as Armadas, 1600-083 Lisboa, Portugal, Department of Chemistry, The Open University, Milton Keynes MK7 6AA, U.K., Wolfson Centre for Rational Structure-Based Design of Molecular Diagnostics, School of Pharmacy & Pharmaceutical Sciences, University of Manchester, Manchester M13 9PL, U.K., and EPSRC National Crystallography Service, School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, U.K."}]},{"given":"Ana Bela","family":"Santana","sequence":"additional","affiliation":[{"name":"CECF, Faculdade de Farm\u00e1cia, Universidade de Lisboa, Av. For\u00e7as Armadas, 1600-083 Lisboa, Portugal, Department of Chemistry, The Open University, Milton Keynes MK7 6AA, U.K., Wolfson Centre for Rational Structure-Based Design of Molecular Diagnostics, School of Pharmacy & Pharmaceutical Sciences, University of Manchester, Manchester M13 9PL, U.K., and EPSRC National Crystallography Service, School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, U.K."}]},{"given":"Jim","family":"Iley","sequence":"additional","affiliation":[{"name":"CECF, Faculdade de Farm\u00e1cia, Universidade de Lisboa, Av. For\u00e7as Armadas, 1600-083 Lisboa, Portugal, Department of Chemistry, The Open University, Milton Keynes MK7 6AA, U.K., Wolfson Centre for Rational Structure-Based Design of Molecular Diagnostics, School of Pharmacy & Pharmaceutical Sciences, University of Manchester, Manchester M13 9PL, U.K., and EPSRC National Crystallography Service, School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, U.K."}]},{"given":"Jo\u00e3o","family":"Neres","sequence":"additional","affiliation":[{"name":"CECF, Faculdade de Farm\u00e1cia, Universidade de Lisboa, Av. For\u00e7as Armadas, 1600-083 Lisboa, Portugal, Department of Chemistry, The Open University, Milton Keynes MK7 6AA, U.K., Wolfson Centre for Rational Structure-Based Design of Molecular Diagnostics, School of Pharmacy & Pharmaceutical Sciences, University of Manchester, Manchester M13 9PL, U.K., and EPSRC National Crystallography Service, School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, U.K."}]},{"given":"Kenneth T.","family":"Douglas","sequence":"additional","affiliation":[{"name":"CECF, Faculdade de Farm\u00e1cia, Universidade de Lisboa, Av. For\u00e7as Armadas, 1600-083 Lisboa, Portugal, Department of Chemistry, The Open University, Milton Keynes MK7 6AA, U.K., Wolfson Centre for Rational Structure-Based Design of Molecular Diagnostics, School of Pharmacy & Pharmaceutical Sciences, University of Manchester, Manchester M13 9PL, U.K., and EPSRC National Crystallography Service, School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, U.K."}]},{"given":"Peter N.","family":"Horton","sequence":"additional","affiliation":[{"name":"CECF, Faculdade de Farm\u00e1cia, Universidade de Lisboa, Av. For\u00e7as Armadas, 1600-083 Lisboa, Portugal, Department of Chemistry, The Open University, Milton Keynes MK7 6AA, U.K., Wolfson Centre for Rational Structure-Based Design of Molecular Diagnostics, School of Pharmacy & Pharmaceutical Sciences, University of Manchester, Manchester M13 9PL, U.K., and EPSRC National Crystallography Service, School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, U.K."}]},{"given":"Michael B.","family":"Hursthouse","sequence":"additional","affiliation":[{"name":"CECF, Faculdade de Farm\u00e1cia, Universidade de Lisboa, Av. For\u00e7as Armadas, 1600-083 Lisboa, Portugal, Department of Chemistry, The Open University, Milton Keynes MK7 6AA, U.K., Wolfson Centre for Rational Structure-Based Design of Molecular Diagnostics, School of Pharmacy & Pharmaceutical Sciences, University of Manchester, Manchester M13 9PL, U.K., and EPSRC National Crystallography Service, School of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, U.K."}]}],"member":"316","published-online":{"date-parts":[[2005,7,6]]},"reference":[{"key":"jm0501331b00001\/jm0501331b00001_1","doi-asserted-by":"crossref","first-page":"770","DOI":"10.1084\/jem.141.4.709","volume":"141","author":"Dewald B.","year":"1975","journal-title":"J. Exp. Med."},{"key":"jm0501331b00002\/jm0501331b00002_1","doi-asserted-by":"crossref","first-page":"49","DOI":"10.1111\/j.1749-6632.1991.tb17005.x","volume":"624","author":"Snider G. L.","year":"1991","journal-title":"Ann. N. Y. Acad. Sci."},{"key":"jm0501331b00003\/jm0501331b00003_1","doi-asserted-by":"crossref","first-page":"266","DOI":"10.1111\/j.1749-6632.1991.tb17024.x","volume":"624","author":"Stockley R. A.","year":"1991","journal-title":"Ann. N. Y. Acad. Sci."},{"key":"jm0501331b00004\/jm0501331b00004_1","doi-asserted-by":"crossref","first-page":"10","DOI":"10.1016\/S0014-2999(02)02182-9","volume":"451","author":"Kawabata K.","year":"2002","journal-title":"Eur. J. Pharmacol."},{"key":"jm0501331b00005\/jm0501331b00005_1","first-page":"34","volume":"1","author":"Anderson G. P.","year":"1999","journal-title":"Curr. Opin. Anti-Inflammatory Immunomodulatory Invest. Drugs"},{"key":"jm0501331b00006\/jm0501331b00006_1","first-page":"280","volume":"343","author":"Barnes P. J","year":"2000","journal-title":"N. Engl. J. Med."},{"key":"jm0501331b00007\/jm0501331b00007_1","first-page":"204","volume":"29","author":"Hastla D. J.","year":"1994","journal-title":"Annu. Rep. Med. Chem."},{"key":"jm0501331b00008\/jm0501331b00008_1","first-page":"120","volume":"31","author":"Bernstein P. R.","year":"1994","journal-title":"Prog. Med. Chem."},{"key":"jm0501331b00009\/jm0501331b00009_1","doi-asserted-by":"crossref","first-page":"1472","DOI":"10.1021\/cr960370z","volume":"97","author":"Babine R. E.","year":"1997","journal-title":"Chem. Rev."},{"key":"jm0501331b00010\/jm0501331b00010_1","doi-asserted-by":"crossref","first-page":"341","DOI":"10.1021\/jm990412m","volume":"43","author":"Leung D.","year":"2000","journal-title":"J. Med. Chem."},{"key":"jm0501331b00011\/jm0501331b00011_1","first-page":"5638","volume":"56","author":"Page M. I.","year":"2000","journal-title":"Tetrahedron"},{"key":"jm0501331b00012\/jm0501331b00012_1","doi-asserted-by":"crossref","first-page":"194","DOI":"10.1038\/322192a0","volume":"322","author":"Doherty J. B.","year":"1986","journal-title":"Nature"},{"key":"jm0501331b00013\/jm0501331b00013_1","doi-asserted-by":"crossref","first-page":"2521","DOI":"10.1021\/jm00171a028","volume":"33","author":"Doherty J. B.","year":"1990","journal-title":"J. Med. Chem."},{"key":"jm0501331b00014\/jm0501331b00014_1","doi-asserted-by":"crossref","first-page":"2528","DOI":"10.1021\/jm00171a029","volume":"33","author":"Finke P. E.","year":"1990","journal-title":"J. Med. Chem."},{"key":"jm0501331b00015\/jm0501331b00015_1","doi-asserted-by":"crossref","first-page":"2535","DOI":"10.1021\/jm00171a031","volume":"33","author":"Shah S. K.","year":"1990","journal-title":"J. Med. Chem."},{"key":"jm0501331b00016\/jm0501331b00016_1","doi-asserted-by":"crossref","first-page":"82","DOI":"10.1038\/327079a0","volume":"327","author":"Navia M. A.","year":"1987","journal-title":"Nature"},{"key":"jm0501331b00017\/jm0501331b00017_1","first-page":"3754","volume":"35","author":"Shah S. K.","year":"1992","journal-title":"J. Med. Chem."},{"key":"jm0501331b00018\/jm0501331b00018_1","doi-asserted-by":"crossref","first-page":"777","DOI":"10.1021\/jm00058a015","volume":"36","author":"Hagmann W. K.","year":"1993","journal-title":"J. Med. Chem."},{"key":"jm0501331b00019\/jm0501331b00019_1","doi-asserted-by":"crossref","first-page":"2462","DOI":"10.1021\/jm00013a021","volume":"38","author":"Finke P. E.","year":"1995","journal-title":"J. Med. Chem."},{"key":"jm0501331b00020\/jm0501331b00020_1","doi-asserted-by":"crossref","first-page":"1068","DOI":"10.1016\/S0960-894X(01)00131-7","volume":"11","author":"Clemente A.","year":"2001","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"jm0501331b00021\/jm0501331b00021_1","first-page":"210","volume":"23","author":"Page M. I","year":"1987","journal-title":"Adv. Phys. Org. Chem."},{"key":"jm0501331b00022\/jm0501331b00022_1","doi-asserted-by":"crossref","first-page":"3367","DOI":"10.1021\/jo0358123","volume":"69","author":"Valente E.","year":"2004","journal-title":"J. Org. Chem."},{"key":"jm0501331b00023\/jm0501331b00023_1","first-page":"1192","volume":"1185","author":"Proctor P.","year":"1982","journal-title":"J. Chem. Soc., Perkin Trans. 2"},{"key":"jm0501331b00024\/jm0501331b00024_1","unstructured":"Perrin, D. D.; Dempsey, B.; Serjeant, E. P. pKaPrediction for Organic Acids and Bases; Chapman and Hall:\u2009 London, 1981. Using the assumptions set out on pp 38\u221240 of this reference, together with the equation pKa= 10.59 \u2212 3.23\u2211\u03c3* derived for the dissociation of R\u2018R\u2018\u2009\u2018NH2+, we calculated pKavalues of 0.71 and \u22120.57 for the conjugated ammonium salts of HO2CCEt2CH(OPh)NHCH(CO2Et)OCOMe and HO2CCEt2CH(SO2Ph)NHCH(CO2Et)OCOMe, respectively. The requisite \u03c3* values are as follows:\u2009 R\u2018 = \u2212CH(OPh)CEt2CO2H, 1.24; \u2212CH(SO2Ph)CEt2CO2H, 1.62; R\u2018\u2009\u2018 = \u2212CH(CO2Et)OCOMe, 1.82."},{"key":"jm0501331b00025\/jm0501331b00025_1","first-page":"99","volume":"58","author":"Clark-Lewis J. W.","year":"1958","journal-title":"Chem. Rev."},{"key":"jm0501331b00026\/jm0501331b00026_1","volume-title":"Asymmetric Synthesis of (R)-(\u2212)-Chlozolinate Through a Chemoenzymatic Procedure. Tetrahedron:\u2009 Asymmetry","author":"Guanti G.","year":"2001"},{"key":"jm0501331b00027\/jm0501331b00027_1","doi-asserted-by":"crossref","first-page":"5657","DOI":"10.1021\/jo00308a028","volume":"55","author":"Gu H.","year":"1990","journal-title":"J. Org. Chem."},{"key":"jm0501331b00028\/jm0501331b00028_1","first-page":"1452","volume":"1450","author":"Branch C. L.","year":"1978","journal-title":"J. Chem. Soc., Perkin Trans. 1"},{"key":"jm0501331b00029\/jm0501331b00029_1","unstructured":"Crystal data for the minor diastereomeric pair6d. A suitable crystal was selected, and data were collected on a Bruker Nonius KappaCCD area detector at the window of a Bruker Nonius FR591 rotating anode (\u03bbMo\u2009K\u03b1= 0.710\u200973 \u00c5) driven by COLLECT and DENZO software at 120 K. The structure was determined in SHELXS-97 and refined using SHELXL-97. C23H24N2O6S,M= 456.50, monoclinic, space group =P21\/n,a= 12.4900(8) \u00c5, 17.5457(13) \u00c5,c= 20.2917(12) \u00c5,\u03b2= 101.760(4)\u00b0,U= 4353.5(5) \u00c53,T= 120(2) K,Z= 8, \u03bc(Mo K\u03b1) = 0.192 mm-1, 38\u2009243 reflections measured, 9874 unique (Rint= 0.1287), which were used in all calculations. FinalR1= 0.0680,wR2= 0.1246 [F2> 2\u03c3(F2)],R1= 0.2052,wR2= 0.1654 (all data). The crystallographic data (excluding structure factors) for the minor diastereomeric pair6dhave been deposited with the Cambridge Crystallographic Data Centre as supplementary publication 4870 numbers CCDC262210. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, U.K. (Fax +44(0)-1223-336033 or e-mail deposit@ ccdc.cam.ac.uk)."},{"key":"jm0501331b00030\/jm0501331b00030_1","doi-asserted-by":"crossref","first-page":"3249","DOI":"10.1016\/S0021-9258(18)50153-8","volume":"237","author":"Kitz R.","year":"1962","journal-title":"J. Biol. Chem."},{"key":"jm0501331b00031\/jm0501331b00031_1","doi-asserted-by":"crossref","first-page":"2605","DOI":"10.1021\/ja952589l","volume":"118","author":"Lightstone F. C.","year":"1996","journal-title":"J. Am. Chem. Soc."},{"key":"jm0501331b00032\/jm0501331b00032_1","doi-asserted-by":"crossref","first-page":"1005","DOI":"10.1021\/ja00342a059","volume":"105","author":"Wipff G.","year":"1983","journal-title":"J. Am. Chem. Soc."},{"key":"jm0501331b00033\/jm0501331b00033_1","first-page":"6471","volume":"66","author":"Chung S. J.","year":"2001","journal-title":"J. Org. Chem."},{"key":"jm0501331b00034\/jm0501331b00034_1","unstructured":"Sybyl 6.8, Tripos Inc.\u2009 St. Louis, MO, 2001."},{"key":"jm0501331b00035\/jm0501331b00035_1","first-page":"4032","volume":"254","author":"Nakajima K.","year":"1979","journal-title":"J. Biol. Chem."},{"key":"jm0501331b00036\/jm0501331b00036_1","first-page":"729","volume":"20","author":"Halgren T","year":"1999","journal-title":"J. Comput. Chem."},{"key":"jm0501331b00037\/jm0501331b00037_1","doi-asserted-by":"crossref","first-page":"11","DOI":"10.1073\/pnas.86.1.7","volume":"86","author":"Navia M. A.","year":"1989","journal-title":"Proc. Natl. Acad. Sci. U.S.A."},{"key":"jm0501331b00038\/jm0501331b00038_1","first-page":"56","volume":"8","author":"Vriend G.","year":"1990","journal-title":"J. Mol. 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