NAI-108

Lantibiotic NAI 108 A1/A2 Mixture

White to off-white powder.

1820892-86-1

32160000

solid

Keep cool and dry.Protect from light.Protect from light when in solution.

InChI=1S/C94H127BrN26O26S5/c1-9-51(107-90(143)72(97)43(4)5)78(131)113-60-37-150-39-62(115-80(133)53(24-42(2)3)108-76(129)44(6)104-79(132)55(110-85(60)138)26-48-29-99-52-18-17-49(95)27-50(48)52)87(140)119-74-46(8)152-41-63(106-71(128)33-102-89(142)65-16-13-21-120(65)94(74)147)88(141)118-73(45(7)122)91(144)117-64-40-151-38-61-86(139)116-59-34-148-23-20-98-77(130)57(112-81(134)54(109-84(59)137)25-47-14-11-10-12-15-47)35-149-36-58(83(136)111-56(28-67(96)124)82(135)114-61)105-70(127)32-101-68(125)30-100-69(126)31-103-92(145)75-66(123)19-22-121(75)93(64)146/h9-12,14-15,17-18,20,23,27,29,42-43,45-46,53-66,72-75,99,122-123H,6,13,16,19,21-22,24-26,28,30-41,97H2,1-5,7-8H3,(H2,96,124)(H,98,130)(H,100,126)(H,101,125)(H,102,142)(H,103,145)(H,104,132)(H,105,127)(H,106,128)(H,107,143)(H,108,129)(H,109,137)(H,110,138)(H,111,136)(H,112,134)(H,113,131)(H,114,135)(H,115,133)(H,116,139)(H,117,144)(H,118,141)(H,119,140)/b23-20-,51-9-/t45-,46+,53+,54-,55+,56+,57+,58-,59+,60-,61+,62+,63+,64-,65+,66+,72+,73-,74-,75+/m1/s1

UGAXZQVTKAPZLB-WCMIHIHVSA-N

Chemical. CAS: 1820892-86-1. Formula: C94H127BrN26O27S5 (A1), C94H127BrN26O26S5 (A2). MW: 2293.4 (A1; R=OH)2277.4 (A2; R=H). Isolated from Actinoallomurus sp. Antibacterial class I lantibiotic. Brominated variant of NAI-107. Inhibits cell wall synthesis and consequently bacterial growth by forming a complex with lipid intermediate II (Lipid II), a key intermediate in peptidoglycan biosynthesis. Efficiently interfers with late stages of cell wall biosynthesis leading to accumulation of the soluble peptidoglycan precursor UDP-N-acetylmuramic acid-pentapeptide (UDP-MurNAc-pentapeptide) in the cytoplasm. Slightly higher activity than NAI-107 against multidrug-resistant Gram-positive pathogens.

N/A

C94H127BrN26O27S5 (A1) C94H127BrN26O26S5 (A2)

2293.4 (A1; R=OH)2277.4 (A2; R=H)

Purity Note: The purity is referred exclusively to the main congener(s), the sample also contains minor related congeners. See: Brominated Variant of the Lantibiotic NAI-107 with Enhanced Antibacterial Potency: J.C. Cruz, et al.; J. Nat. Prod. 78, 2642 (2015)

Vial

Antibacterial class I lantibiotic. Brominated variant of NAI-107 (AG-CN2-0307 https://adipogen.com/ag-cn2-0307-nai-107-microbisporicin.html ). Inhibits cell wall synthesis and consequently bacterial growth by forming a complex with lipid intermediate II (Lipid II), a key intermediate in peptidoglycan biosynthesis. Efficiently interfers with late stages of cell wall biosynthesis leading to accumulation of the soluble peptidoglycan precursor UDP-N-acetylmuramic acid-pentapeptide (UDP-MurNAc-pentapeptide) in the cytoplasm. Slightly higher activity than NAI-107 against multidrug-resistant Gram-positive pathogens.

>80% (HPLC, for A1/A2)

O=C(N[C@H](C(NC(C(N[C@H](C(N[C@H](C(N[C@H]([C@H](C)SC[C@@H](C(N[C@H]([C@H](O)C)C(N[C@@H](C(N1[C@H]2[C@@H](O)CC1)=O)CSC[C@H](NC([C@H](CC(N)=O)NC([C@H](NC(CNC(CNC(CNC2=O)=O)=O)=O)CSC[C@@H](C(N/C=CSC3)=O)NC4=O)=O)=O)C(N[C@@H]3C(N[C@@H]4CC5=CC=CC=C5)=O)=O)=O)=O)NC6=O)C(N7[C@H](C(NC6)=O)CCC7)=O)=O)CSC8)=O)CC(C)C)=O)=C)=O)CC9=CNC%10=C9C=C(Br)C=C%10)[C@@H]8NC(/C(NC([C@H](C(C)C)N)=O)=C/C)=O

Soluble in DMSO, aqueous acetonitrile or ethanol.

Isolated from Actinoallomurus sp.

Non-hazardous

Natural Products/Extracts

12352200

Stable for at least 2 years after receipt when stored at -20°C.