Description

Chemical structure: peptide

Product Details

CAS Number

1414-45-5

Source

Lactococcus lactis

Linear Formula

C₁₄₃H₂₃₀N₄₂O₃₇S₇

Application

Nisin is a polycyclic lantibiotic produced by Lactococcus lactis. It is commonly used as a food preservative. It is also used as a selective agent in cell culture for the isolation of gram-negative bacteria, yeast, and molds. Nisin has been used in bioassays to study posttranslational modification. Used to form targeted pores in cell membranes that are mediated by lipid II. Used to study the assembly and stability of nisin-lipid II pore complexes.

Appearance

powder

Molecular Weight

3354.07

Storage Temp.

2-8 °C

Antibiotic Activity Spectrum

Gram-negative bacteria, Gram-positive bacteria

Mode of Action

cell membrane/interferes

SMILES

[H]N[C@@H] ([C@@H] (C)CC)C (=O)N\C (=C\C)C (=O)N[C@H]1CSC[C@H] (NC (=O)[C@H] (CC (C)C)NC (=O)C (=C)NC (=O)[C@@H] (NC1=O)[C@@H] (C)CC)C (=O)N[C@H]2[C@H] (C)SC[C@H] (NC (=O)CNC (=O)[C@@H]3CCCN3C2=O)C (=O)N[C@H] (CCCCN)C (=O)N[C@@H]4[C@@H] (C)SC[C@H] (NC (=O)CNC (=O)[C@H] (CCSC)NC (=O)[C@H] (CC (C)C)NC (=O)[C@H] (C)NC (=O)CNC4=O)C (=O)N[C@@H] (CC (N)=O)C (=O)N[C@@H] (CCSC)C (=O)N[C@@H] (CCCCN)C (=O)N[C@H]5[C@H] (C)SC[C@@H]6NC (=O)[C@@H] (NC (=O)[C@H] (C)NC5=O)[C@H] (C)SC[C@H] (NC (=O)[C@H] (Cc7cnc[nH]7)NC6=O)C (=O)N[C@@H] (CO)C (=O)N[C@@H] ([C@@H] (C)CC)C (=O)N[C@@H] (Cc8cnc[nH]8)C (=O)N[C@@H] (C (C)C)C (=O)NC (=C)C (=O)N[C@@H] (CCCCN)C (O)=O

InChI

1S/C143H230N42O37S7/c1-24-69 (11)105 (148)135 (213)162-82 (27-4)118 (196)174-94-58-225-59-95 (175-123 (201)89 (48-67 (7)8)169-115 (193)74 (16)158-138 (216)107 (70 (12)25-2)180-132 (94)210)133 (211)184-112-79 (21)229-61-96 (160-104 (190)56-152-134 (212)100-38-34-44-185 (100)142 (112)220)128 (206)164-84 (36-29-32-42-145)120 (198)182-109-76 (18)226-60-97 (161-103 (189)55-151-117 (195)85 (39-45-223-22)165-122 (200)88 (47-66 (5)6)168-113 (191)72 (14)156-102 (188)54-153-136 (109)214)129 (207)171-92 (51-101 (147)187)125 (203)166-86 (40-46-224-23)119 (197)163-83 (35-28-31-41-144)121 (199)183-110-77 (19)228-63-99-130 (208)170-90 (49-80-52-149-64-154-80)124 (202)176-98 (62-227-78 (20)111 (141 (219)177-99)181-116 (194)75 (17)159-140 (110)218)131 (209)173-93 (57-186)127 (205)179-108 (71 (13)26-3)139 (217)172-91 (50-81-53-150-65-155-81)126 (204)178-106 (68 (9)10)137 (215)157-73 (15)114 (192)167-87 (143 (221)222)37-30-33-43-146/h27,52-53,64-72,75-79,83-100,105-112,186H,15-16,24-26,28-51,54-63,144-146,148H2,1-14,17-23H3, (H2,147,187) (H,149,154) (H,150,155) (H,151,195) (H,152,212) (H,153,214) (H,156,188) (H,157,215) (H,158,216) (H,159,218) (H,160,190) (H,161,189) (H,162,213) (H,163,197) (H,164,206) (H,165,200) (H,166,203) (H,167,192) (H,168,191) (H,169,193) (H,170,208) (H,171,207) (H,172,217) (H,173,209) (H,174,196) (H,175,201) (H,176,202) (H,177,219) (H,178,204) (H,179,205) (H,180,210) (H,181,194) (H,182,198) (H,183,199) (H,184,211) (H,221,222)/b82-27+/t69-,70-,71-,72-,75-,76?,77?,78?,79?,83-,84+,85-,86-,87-,88-,89-,90-,91-,92-,93-,94-,95-,96-,97-,98-,99-,100-,105-,106-,107-,108-,109+,110-,111-,112-/m0/s1

InChI key

NVNLLIYOARQCIX-ILAIHEEGSA-N

Handling Precaution

Nisin binds to cell wall precursor lipid components of bacteria and disrupts cell wall production. Nisin alters the cell membrane which results in the leakage of cytoplasmic components and destruction of the proton motive force.
Nisin is an antibiotic with bactericidal action. It binds to the lipid A portion of bacterial lipopolysaccharides and induces pore formation in the membranes of cortex cells from excised sorghum roots.
Mode of Action: Binds to and interferes with the permeability of the cytoplasmic membrane.
Antimicrobial spectrum: Gram-negative and Gram-positive bacteria (requires chelator such as EDTA).