{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,17]],"date-time":"2025-10-17T13:29:34Z","timestamp":1760707774330,"version":"build-2065373602"},"reference-count":50,"publisher":"Wiley","issue":"9","license":[{"start":{"date-parts":[[2007,1,19]],"date-time":"2007-01-19T00:00:00Z","timestamp":1169164800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Eur J Org Chem"],"published-print":{"date-parts":[[2007,3]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Several widely used antibiotics such as \u03b2\u2010lactams, glycopeptides, and lipoglycopeptides exhibit their activity by interfering with peptidoglycan biosynthesis. Ever\u2010increasingresistance to these and other agents has placed a renewed emphasis on the need to understand the reactions in this biosynthetic pathway at the molecular level. While efficientaccess to many of the biosynthetic enzymes has been gained, the isolation of their natural substrates has proven difficult. Chemical synthesis has provided valuable tools to circumvent this problem and has allowed convenient access to several key intermediates and analogs thereof. Recent advances in the synthesis of the late\u2010stage intermediates, including the Park nucleotide, lipid I, lipid II, fragments of the bacterial cell wall, along with other biochemical probes are reviewed. A brief discussion on the use of these substrates in study of this important biosynthetic pathway is also included. (\u00a9 Wiley\u2010VCH Verlag GmbH &amp; Co. KGaA, 69451 Weinheim, Germany, 2007)<\/jats:p>","DOI":"10.1002\/ejoc.200600750","type":"journal-article","created":{"date-parts":[[2007,1,19]],"date-time":"2007-01-19T04:50:58Z","timestamp":1169182258000},"page":"1399-1414","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":21,"title":["Synthesis of Substrates and Biochemical Probes for Study of the Peptidoglycan Biosynthetic Pathway"],"prefix":"10.1002","volume":"2007","author":[{"given":"Radha S.","family":"Narayan","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Michael S.","family":"VanNieuwenhze","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2007,3,2]]},"reference":[{"key":"e_1_2_7_1_2","doi-asserted-by":"publisher","DOI":"10.1039\/np9920900199"},{"key":"e_1_2_7_2_2","doi-asserted-by":"publisher","DOI":"10.1128\/MMBR.62.1.181-203.1998"},{"key":"e_1_2_7_3_2","unstructured":"In Gram negative bacteria and some Gram positives meso\u2010diaminolimelic acid (meso\u2010DAP) is incorporated in place ofL\u2010Lys (see refs 1 2)."},{"key":"e_1_2_7_4_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0021-9258(18)55843-9"},{"key":"e_1_2_7_5_2","unstructured":"In some Gram\u2010positive bacteria 1\u20135 amino acid residues may be attached to the \u03f5\u2010amino group of the lysine (ormeso\u2010DAP) residue. These are typically glycine although organisms incorporatingL\u2010serine L\u2010threonine and other amino acids are known (see ref.[2])."},{"volume-title":"The Molecular Basis of Antibiotic Action","year":"1981","author":"Gale E. F.","key":"e_1_2_7_6_2"},{"key":"e_1_2_7_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/jm960294s"},{"key":"e_1_2_7_8_2","doi-asserted-by":"publisher","DOI":"10.1128\/jb.174.11.3549-3557.1992"},{"key":"e_1_2_7_9_2","doi-asserted-by":"publisher","DOI":"10.1016\/S1367-5931(02)00355-1"},{"key":"e_1_2_7_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja973172d"},{"key":"e_1_2_7_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja01464a035"},{"key":"e_1_2_7_12_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja00059a023"},{"key":"e_1_2_7_13_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja011708w"},{"key":"e_1_2_7_14_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja010028q"},{"key":"e_1_2_7_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja016082o"},{"key":"e_1_2_7_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja974221p"},{"key":"e_1_2_7_17_2","doi-asserted-by":"publisher","DOI":"10.1021\/bi00764a002"},{"key":"e_1_2_7_18_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(00)97097-7"},{"key":"e_1_2_7_19_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0008-6215(00)85534-2"},{"key":"e_1_2_7_20_2","doi-asserted-by":"publisher","DOI":"10.1016\/0960-894X(95)00460-B"},{"key":"e_1_2_7_21_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja017386d"},{"key":"e_1_2_7_22_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja0166848"},{"key":"e_1_2_7_23_2","unstructured":"The syntheses also differ with respect to the identity of the second amino acid residue in the stem peptide. In the Schwartz synthesis this residue is a \u03b3\u2010D\u2010Glu while in the VanNieuwenhze synthesis it is \u03b3\u2010D\u2010Gln."},{"key":"e_1_2_7_24_2","unstructured":"The protecting group schemes illustrated in Scheme\u00a08 reflect those utilized in both of the reported synthetic routes to lipid II."},{"key":"e_1_2_7_25_2","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.60.2205"},{"key":"e_1_2_7_26_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0008-6215(00)81509-8"},{"key":"e_1_2_7_27_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol016692t"},{"key":"e_1_2_7_28_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4039(94)02348-F"},{"key":"e_1_2_7_29_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja982232s"},{"key":"e_1_2_7_30_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo035397e"},{"key":"e_1_2_7_31_2","doi-asserted-by":"publisher","DOI":"10.1021\/jo035583k"},{"key":"e_1_2_7_32_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.mib.2003.08.004"},{"key":"e_1_2_7_33_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.bcp.2005.10.029"},{"key":"e_1_2_7_34_2","doi-asserted-by":"publisher","DOI":"10.1038\/nrd2004"},{"key":"e_1_2_7_35_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr030106n"},{"key":"e_1_2_7_36_2","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.34.3.413"},{"key":"e_1_2_7_37_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja035217i"},{"key":"e_1_2_7_38_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja021097n"},{"key":"e_1_2_7_39_2","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.42.1.154"},{"key":"e_1_2_7_40_2","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.39.3.714"},{"key":"e_1_2_7_41_2","doi-asserted-by":"publisher","DOI":"10.1128\/AAC.45.6.1823-1827.2001"},{"key":"e_1_2_7_42_2","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.45.839"},{"volume-title":"Nisin and Novel Lantibiotics","year":"1991","author":"Limbert M. 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