Actagardin

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 peptide lantibiotic made by Actinoplanes brasiliensis. It was discovered in 1975 by Lepetit S.p.A. Its method of antibiotic activity involves the inhibition of peptidoglycan, preferentially targeting gram negative bacteria. It has become the subject of recent renewed inteterst in the fight against antibiotic resistant bacteria, particularly in the treatment of Streptococcus and Clostridioides difficile, though no pharmaceutical manufacturer is currently known to be pursuing commercialization.

References

  1. 1 2 "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.
  4. ↑ Ramírez-Rendón, Dulce; Guzmán-Chávez, Fernando; García-Ausencio, Carlos; Rodríguez-Sanoja, Romina; Sánchez, Sergio (2023-12-01). "The untapped potential of actinobacterial lanthipeptides as therapeutic agents". Molecular Biology Reports. 50 (12): 10605–10616. doi:10.1007/s11033-023-08880-w. ISSN 1573-4978. PMC 10676316. PMID 37934370.