Actagardin

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Actagardin
Names
Systematic IUPAC name
(2R,5S,8R,11S,14S,17R,23R,26R,32R,35S,38R,41R,44R)-44-{(2S,3S)-2-[(2R)-2-{(2S)-2-[(2R)-2-Aminopropanamido]-4-methylpentanamido}butanamido]-3-methylpentanamido}-11-[(2S)-butan-2-yl]-17,41-diethyl-26-(hydroxymethyl)-32-[(1H-indol-3-yl)methyl]-2,5,8,23,38-pentamethyl-4,7,10,13,16,19,22,25,28,31,34,38,40,43-tetradecaoxo-14,35-di(propan-2-yl)-3,6,9,12,15,18,21,24,27,30,33,37,39,42-tetradecaazaheptatetracontanedioic acid
Other names
Gardimycin
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C81H132N20O23/c1-20-40(12)63(79(121)89-45(17)67(109)86-44(16)68(110)90-47(19)81(123)124)101-78(120)62(39(10)11)99-72(114)50(22-3)91-58(103)34-84-66(108)43(15)87-76(118)57(36-102)92-59(104)35-85-70(112)56(32-48-33-83-53-28-26-25-27-49(48)53)97-77(119)61(38(8)9)98-69(111)46(18)88-71(113)51(23-4)93-74(116)54(29-30-60(105)106)95-80(122)64(41(13)21-2)100-73(115)52(24-5)94-75(117)55(31-37(6)7)96-65(107)42(14)82/h25-28,33,37-47,50-52,54-57,61-64,83,102H,20-24,29-32,34-36,82H2,1-19H3,(H,84,108)(H,85,112)(H,86,109)(H,87,118)(H,88,113)(H,89,121)(H,90,110)(H,91,103)(H,92,104)(H,93,116)(H,94,117)(H,95,122)(H,96,107)(H,97,119)(H,98,111)(H,99,114)(H,100,115)(H,101,120)(H,105,106)(H,123,124)/t40-,41-,42+,43+,44-,45+,46+,47+,50+,51+,52+,54+,55-,56+,57+,61-,62-,63-,64-/m0/s1
    Key: LAWKVNVCUPIOMG-HWWYPGLISA-N
  • InChI=1/C81H132N20O23/c1-20-40(12)63(79(121)89-45(17)67(109)86-44(16)68(110)90-47(19)81(123)124)101-78(120)62(39(10)11)99-72(114)50(22-3)91-58(103)34-84-66(108)43(15)87-76(118)57(36-102)92-59(104)35-85-70(112)56(32-48-33-83-53-28-26-25-27-49(48)53)97-77(119)61(38(8)9)98-69(111)46(18)88-71(113)51(23-4)93-74(116)54(29-30-60(105)106)95-80(122)64(41(13)21-2)100-73(115)52(24-5)94-75(117)55(31-37(6)7)96-65(107)42(14)82/h25-28,33,37-47,50-52,54-57,61-64,83,102H,20-24,29-32,34-36,82H2,1-19H3,(H,84,108)(H,85,112)(H,86,109)(H,87,118)(H,88,113)(H,89,121)(H,90,110)(H,91,103)(H,92,104)(H,93,116)(H,94,117)(H,95,122)(H,96,107)(H,97,119)(H,98,111)(H,99,114)(H,100,115)(H,101,120)(H,105,106)(H,123,124)/t40-,41-,42+,43+,44-,45+,46+,47+,50+,51+,52+,54+,55-,56+,57+,61-,62-,63-,64-/m0/s1
    Key: LAWKVNVCUPIOMG-HWWYPGLIBM
  • CC[C@H](C)[C@@H](C(=O)N[C@H](CCC(=O)O)C(=O)N[C@H](CC)C(=O)N[C@H](C)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](CC1=CNC2=CC=CC=C21)C(=O)NCC(=O)N[C@H](CO)C(=O)N[C@H](C)C(=O)NCC(=O)N[C@H](CC)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H](C)C(=O)N[C@@H](C)C(=O)N[C@H](C)C(=O)O)NC(=O)[C@@H](CC)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C)N
Properties
C81H132N20O23
Molar mass 1754.064 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Actagardin (INN; also known as gardimycin) is a tetracyclic[1] peptide lantibiotic made by Actinoplanes brasiliensis.[2] It was discovered in 1975 by Lepetit S.p.A.[3] Its method of antibiotic activity involves the inhibition of peptidoglycan, preferentially targeting gram negative bacteria.[1]

References

  1. ^ a b "Actagardin (CAS 59165-34-3)". www.caymanchem.com. Retrieved 2022-11-07.
  2. ^ Terekhova LP, Galatenko OA, Laĭko AV, Sumarukova IG, Golova TP, Tolstykh IV, Kozlova I (1999). "[Actinoplanes brasiliensis INA 3802--a producer of peptide antibiotics]". Antibiotiki i Khimioterapiia. 44 (4): 5–8. PMID 10483488.
  3. ^ Somma S, Merati W, Parenti F (March 1977). "Gardimycin, a new antibiotic inhibiting peptidoglycan synthesis". Antimicrobial Agents and Chemotherapy. 11 (3): 396–401. doi:10.1128/AAC.11.3.396. PMC 351996. PMID 404960.


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