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PRD_000225

Summary
Name:GE2270a
Formula:C56 H58 N15 O10 S6
Fomular weight:1293.544
Component type:peptide-like
Polymer sequences:SER, BB9, MEN, BB6, VAL, BB7, GLY, BB8, BB9, BB9, MH6, BB9, SER, PRO, NH2
Non-polymer components:
BIRD class:Antibiotic
Represented as:polymer
Compound Details:GEA2270A is a member of a sulphur-rich heterocyclic peptides class. All members share a macrocylic core, consisting of a nitrogen containing, six-membered ring central to dehydroamino acids and a subset of five member ring structures including thiazoles, thiazolines and oxazoles. Post translational maturation of thiazole and oxazole containing antibiotics involves the enzymic condensation of a Cys or Ser with the alpha- carbonyl of the preceding amino acid to form a thioether or ether bond, then dehydration to form a double bond with the alpha-amino nitrogen. Thiazoline or oxazoline ring are dehydrogenated to form thiazole or oxazole rings. In addition cross-linking of a Ser and a Cys-Ser pair usually separated by 7 or 8 residues along the peptide chain produce a pyridinyl ring. The Ser residues are dehydrated to didehydroalanines, then bonded between their beta carbons. The alpha carbonyl of the Cys condenses with alpha carbon of the first Ser to form a pyridinyl ring. The ring may be mutiply dehydrogenated to form a pyridine ring with loss of the amino nitrogen of the first Ser. Several isomers are produced. The structural differences between them lie in the extent of the modifications, methylation, methoxylation, and oxidation of the thiazole and oxazole rings, and methylation of asparagine. The amidation of Pro-14 probably does not occur by the same mechanism, oxidative cleavage of glycine, as in eukaryotes.
Description:GEA2270A IS A THIOPEPTIDE CONSISTING OF ONE PYRIDINE, ONE OXAZOLE AND FIVE THIAZOLE RINGS. THE OBSERVED C-TERMINAL AMINO GROUP NH2(15) IS LIKELY TO BE A POST-TRANSLATIONAL DECARBOXYLATED REMNANT OF A SER C-TERMINAL RESIDUE.
Families:FAM_000096

Chemical Descriptors

TypeProgramVersionDescriptor
InChIInChI1.03InChI=1S/C56H58N15O10S6/c1-24(2)39-55-70-42(36(87-55)19-80-5)47(77)59-17-38(73)67-43(44(74)26-10-7-6-8-11-26)54-66-34(23-85-54)52-63-31(20-83-52)41-27(50-64-32(21-82-50)46(76)61-29(16-37(72)58-4)53-69-40(25(3)86-53)48(78)68-39)13-14-28(60-41)51-65-33(22-84-51)49-62-30(18-81-49)56(79)71-15-9-12-35(71)45(57)75/h6-8,10-11,20-24,27,29-30,35,39,43-44,74H,9,12-19H2,1-5H3,(H2,57,75)(H,58,72)(H,59,77)(H,61,76)(H,67,73)(H,68,78)
InChIKeyInChI1.03UMPNWRLEAJXFKB-UHFFFAOYSA-N
SMILES_CANONICALCACTVS3.370CNC(=O)C[C@@H]1NC(=O)c2csc(n2)[C@H]3CC[C](=[N]=[C]3c4csc(n4)c5csc(n5)[C@@H](NC(=O)CNC(=O)c6nc(sc6COC)[C@@H](NC(=O)c7nc1sc7C)C(C)C)[C@H](O)c8ccccc8)c9scc(n9)C%10=N[C@@H](CO%10)C(=O)N%11CCC[C@H]%11C(N)=O
SMILESCACTVS3.370CNC(=O)C[CH]1NC(=O)c2csc(n2)[CH]3CC[C](=[N]=[C]3c4csc(n4)c5csc(n5)[CH](NC(=O)CNC(=O)c6nc(sc6COC)[CH](NC(=O)c7nc1sc7C)C(C)C)[CH](O)c8ccccc8)c9scc(n9)C%10=N[CH](CO%10)C(=O)N%11CCC[CH]%11C(N)=O
SMILES_CANONICALOpenEye OEToolkits1.7.6Cc1c2nc(s1)[C@@H](NC(=O)c3csc(n3)[C@@H]4CCC(=[N]=C4c5csc(n5)-c6csc(n6)[C@@H](NC(=O)CNC(=O)c7c(sc(n7)[C@@H](NC2=O)C(C)C)COC)[C@@H](c8ccccc8)O)c9nc(cs9)C1=N[C@@H](CO1)C(=O)N1CCC[C@H]1C(=O)N)CC(=O)NC
SMILESOpenEye OEToolkits1.7.6Cc1c2nc(s1)C(NC(=O)c3csc(n3)C4CCC(=[N]=C4c5csc(n5)-c6csc(n6)C(NC(=O)CNC(=O)c7c(sc(n7)C(NC2=O)C(C)C)COC)C(c8ccccc8)O)c9nc(cs9)C1=NC(CO1)C(=O)N1CCCC1C(=O)N)CC(=O)NC

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PDB entries from 2024-06-26

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