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Nosiheptide precursor [Cleaved into: Nosiheptide (NOS) (Antibiotic 9671-RP) (Multhiomycin)]

 NOSM_STRAS              Reviewed;          50 AA.
C6FX52;
14-DEC-2011, integrated into UniProtKB/Swiss-Prot.
01-SEP-2009, sequence version 1.
22-NOV-2017, entry version 16.
RecName: Full=Nosiheptide precursor {ECO:0000303|PubMed:19678698};
Contains:
RecName: Full=Nosiheptide {ECO:0000303|PubMed:19678698};
Short=NOS {ECO:0000303|PubMed:19678698};
AltName: Full=Antibiotic 9671-RP {ECO:0000303|PubMed:7379912};
AltName: Full=Multhiomycin {ECO:0000303|PubMed:7038038};
Name=nosM {ECO:0000312|EMBL:ACR48342.1};
Streptomyces actuosus.
Bacteria; Actinobacteria; Streptomycetales; Streptomycetaceae;
Streptomyces.
NCBI_TaxID=1885;
[1] {ECO:0000305, ECO:0000312|EMBL:ACR48342.1}
NUCLEOTIDE SEQUENCE [GENOMIC DNA], HYDROXYLATION AT GLU-43, AND MASS
SPECTROMETRY.
STRAIN=ATCC 25421 / DSM 40337 / JCM 4445 / NBRC 13009 / NRRL 2954 /
VKM Ac-1274 {ECO:0000269|PubMed:19678698};
PubMed=19678698; DOI=10.1021/cb900133x;
Yu Y., Duan L., Zhang Q., Liao R., Ding Y., Pan H.,
Wendt-Pienkowski E., Tang G., Shen B., Liu W.;
"Nosiheptide biosynthesis featuring a unique indole side ring
formation on the characteristic thiopeptide framework.";
ACS Chem. Biol. 4:855-864(2009).
[2] {ECO:0000305}
FUNCTION.
STRAIN=ATCC 25421 / DSM 40337 / JCM 4445 / NBRC 13009 / NRRL 2954 /
VKM Ac-1274 {ECO:0000269|PubMed:7379912};
PubMed=7379912; DOI=10.1007/BF01975121;
Benazet F., Cartier M., Florent J., Godard C., Jung G., Lunel J.,
Mancy D., Pascal C., Renaut J., Tarridec P., Theilleux J., Tissier R.,
Dubost M., Ninet L.;
"Nosiheptide, a sulfur-containing peptide antibiotic isolated from
Streptomyces actuosus 40037.";
Experientia 36:414-416(1980).
[3] {ECO:0000305}
FUNCTION.
STRAIN=ATCC 25421 / DSM 40337 / JCM 4445 / NBRC 13009 / NRRL 2954 /
VKM Ac-1274 {ECO:0000269|PubMed:7038038};
PubMed=7038038; DOI=10.1099/00221287-126-1-185;
Cundliffe E., Thompson J.;
"The mode of action of nosiheptide (multhiomycin) and the mechanism of
resistance in the producing organism.";
J. Gen. Microbiol. 126:185-192(1981).
[4] {ECO:0000305}
FUNCTION.
PubMed=12954336; DOI=10.1016/S1074-5521(03)00173-X;
Lentzen G., Klinck R., Matassova N., Aboul-ela F., Murchie A.I.;
"Structural basis for contrasting activities of ribosome binding
thiazole antibiotics.";
Chem. Biol. 10:769-778(2003).
[5] {ECO:0000305}
FUNCTION.
PubMed=18380436; DOI=10.1021/ja710608w;
Baumann S., Schoof S., Harkal S.D., Arndt H.D.;
"Mapping the binding site of thiopeptide antibiotics by proximity-
induced covalent capture.";
J. Am. Chem. Soc. 130:5664-5666(2008).
[6] {ECO:0000305}
FUNCTION.
PubMed=20441189; DOI=10.1021/ja909317n;
Baumann S., Schoof S., Bolten M., Haering C., Takagi M., Shin-ya K.,
Arndt H.D.;
"Molecular determinants of microbial resistance to thiopeptide
antibiotics.";
J. Am. Chem. Soc. 132:6973-6981(2010).
[7] {ECO:0000305}
FUNCTION.
PubMed=21836384; DOI=10.1292/jvms.11-0051;
Okada Y., Okutani A., Suzuki H., Asakura H., Monden S., Nakama A.,
Maruyama T., Igimi S.;
"Antimicrobial susceptibilities of Listeria monocytogenes isolated in
Japan.";
J. Vet. Med. Sci. 73:1681-1684(2011).
[8] {ECO:0000305}
MASS SPECTROMETRY, AND AMIDATION AT SER-49.
STRAIN=ATCC 25421 / DSM 40337 / JCM 4445 / NBRC 13009 / NRRL 2954 /
VKM Ac-1274 {ECO:0000269|PubMed:21047073};
PubMed=21047073; DOI=10.1021/ja106571g;
Yu Y., Guo H., Zhang Q., Duan L., Ding Y., Liao R., Lei C., Shen B.,
Liu W.;
"NosA catalyzing carboxyl-terminal amide formation in nosiheptide
maturation via an enamine dealkylation on the serine-extended
precursor peptide.";
J. Am. Chem. Soc. 132:16324-16326(2010).
[9] {ECO:0000305}
X-RAY CRYSTALLOGRAPHY OF 38-49, AND HYDRATION AT SER-49.
PubMed=893891; DOI=10.1021/ja00461a039;
Pascard C., Ducruix A., Lunel J., Prange T.;
"Highly modified cysteine-containing antibiotics. Chemical structure
and configuration of nosiheptide.";
J. Am. Chem. Soc. 99:6418-6423(1977).
[10] {ECO:0000305}
STRUCTURE BY NMR, AND HYDRATION AT SER-49.
PubMed=2584148;
Mocek U., Chen L.C., Keller P.J., Houck D.R., Beale J.M., Floss H.G.;
"1H and 13C NMR assignments of the thiopeptide antibiotic
nosiheptide.";
J. Antibiot. 42:1643-1648(1989).
[11] {ECO:0000305}
X-RAY CRYSTALLOGRAPHY (3.7 ANGSTROMS) OF 38-49, AND HYDRATION AT
SER-49.
PubMed=18406324; DOI=10.1016/j.molcel.2008.01.009;
Harms J.M., Wilson D.N., Schluenzen F., Connell S.R., Stachelhaus T.,
Zaborowska Z., Spahn C.M., Fucini P.;
"Translational regulation via L11: molecular switches on the ribosome
turned on and off by thiostrepton and micrococcin.";
Mol. Cell 30:26-38(2008).
-!- FUNCTION: Inhibits bacterial protein biosynthesis by binding to
ribosomes. Specifically, binds to the complex of 23S rRNA and
ribosomal protein L11 (RPLK) in the 50S ribosomal subunit. While
allowing a weak binding of elongation factor G (EF-G) to the
ribosome and subsequent GTP-hydrolysis, probably impairs
conformational changes in both the ribosome and EF-G which are
necessary for translocation. In vitro, inhibits Gram-positive
bacteria S.aureus strain 209P (MIC=0.0009 ug/ml), S.aureus strain
133 (MIC=0.0019 ug/ml), S.aureus strain B3 (MIC=0.003 ug/ml),
S.aureus strain Hb (MIC=0.003 ug/ml), M.citreus strain ATCC 8411
(MIC=0.0038 ug/ml), M.lysodeikticus strain ATCC 4698 (MIC=0.003
ug/ml), S.lutea strain ATCC 9341 (MIC=0.0011 ug/ml), S.faecalis
strain ATCC 9790 (MIC=0.0007 ug/ml), S.viridans (MIC=0.0065
ug/ml), S.pyogenes hemolyticus strain Dig7 (MIC=0.00028 ug/ml),
D.pneumoniae strain Til (MIC=0.00015 ug/ml), N.catrrhalis
(MIC=0.0017 ug/ml), L.casei strain ATCC 6633 (MIC=0.003 ug/ml),
B.cereus strain ATCC 6630 (MIC=0.0071 ug/ml) and various isolates
of L.monocytogenes. In vitro, inhibits Gram-negative bacterium
P.multocida strain A125 (MIC=0.0024 ug/ml) but not M.smegmatis
strain ATCC 6630, S.typhimurium, A.aerogenes strain ATCC 8308,
P.vulgaris, K.pneumoniae strain ATCC 10031, S.marcescens strain
A476, P.aeruginosa strain Bass or B.bronchiseptica strain CN387.
Does not inhibit Gram-negative bacterium E.coli strain ATCC 9637
but does inhibit purified ribosomes from E.coli. In vivo, has no
systemic effect in mice infected with staphylococci or
streptococci when applied orally or subcutaneously. Has a local
effect in mice infected subcutaneously or intraperitoneally with
staphylococci when applied immediately afterwards. Is not toxic to
mice. {ECO:0000269|PubMed:12954336, ECO:0000269|PubMed:18380436,
ECO:0000269|PubMed:18406324, ECO:0000269|PubMed:20441189,
ECO:0000269|PubMed:21836384, ECO:0000269|PubMed:7038038,
ECO:0000269|PubMed:7379912}.
-!- PTM: The amidation of Ser-49 is produced by the oxidative cleavage
of Ser-50 rather than of a glycine, as in eukaryotes.
{ECO:0000269|PubMed:21047073}.
-!- MASS SPECTROMETRY: Mass=1269.74; Method=Unknown; Range=38-49;
Evidence={ECO:0000269|PubMed:19678698,
ECO:0000269|PubMed:21047073};
-!- MASS SPECTROMETRY: Mass=1314.1467; Method=Electrospray; Range=38-
49; Evidence={ECO:0000269|PubMed:19678698,
ECO:0000269|PubMed:21047073};
-!- MISCELLANEOUS: The mature peptide is identical to multhiomycin
from S.antibioticus strain 8446CC1 (PMID 681244). {ECO:0000305}.
-!- MISCELLANEOUS: Used as an antibiotic growth promotant in poultry
and pig farming in parts of Asia. {ECO:0000303|PubMed:21836384}.
-!- SIMILARITY: Belongs to the thiocillin family. {ECO:0000255}.
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EMBL; FJ438820; ACR48342.1; -; Genomic_DNA.
PDB; 2ZJP; X-ray; 3.70 A; 5=38-50.
PDBsum; 2ZJP; -.
SMR; C6FX52; -.
EvolutionaryTrace; C6FX52; -.
GO; GO:0070180; F:large ribosomal subunit rRNA binding; IDA:UniProtKB.
GO; GO:0050829; P:defense response to Gram-negative bacterium; IDA:UniProtKB.
GO; GO:0050830; P:defense response to Gram-positive bacterium; IDA:UniProtKB.
GO; GO:0045900; P:negative regulation of translational elongation; IDA:UniProtKB.
InterPro; IPR023895; Thiopep_bacteriocin_prcur.
TIGRFAMs; TIGR03892; thiopep_precurs; 1.
1: Evidence at protein level;
3D-structure; Amidation; Antibiotic; Antimicrobial; Hydroxylation;
Thioether bond.
CHAIN 1 50 Nosiheptide precursor.
/FTId=PRO_0000414621.
PEPTIDE 38 49 Nosiheptide.
{ECO:0000269|PubMed:19678698}.
/FTId=PRO_0000414622.
BINDING 43 43 3-methyl-4-hydroxymethylindole-2-
carboxylic acid (covalent; via 2 links).
{ECO:0000269|PubMed:18406324,
ECO:0000269|PubMed:2584148,
ECO:0000269|PubMed:893891}.
BINDING 45 45 3-methyl-4-hydroxymethylindole-2-
carboxylic acid (covalent; via 2 links).
{ECO:0000269|PubMed:18406324,
ECO:0000269|PubMed:2584148,
ECO:0000269|PubMed:893891}.
MOD_RES 43 43 4-hydroxyglutamate.
{ECO:0000269|PubMed:18406324,
ECO:0000269|PubMed:19678698,
ECO:0000269|PubMed:2584148,
ECO:0000269|PubMed:893891}.
MOD_RES 49 49 2,3-didehydroalanine (Ser).
{ECO:0000269|PubMed:18406324,
ECO:0000269|PubMed:2584148,
ECO:0000269|PubMed:893891}.
MOD_RES 49 49 Serine amide; atypical.
{ECO:0000269|PubMed:18406324,
ECO:0000269|PubMed:21047073,
ECO:0000269|PubMed:2584148,
ECO:0000269|PubMed:893891}.
CROSSLNK 38 47 3-hydroxypyridine-2,5-dicarboxylic acid
(Ser-Ser) (with C-46).
{ECO:0000269|PubMed:18406324,
ECO:0000269|PubMed:2584148,
ECO:0000269|PubMed:893891}.
CROSSLNK 38 46 3-hydroxypyridine-2,5-dicarboxylic acid
(Ser-Cys) (with S-47).
{ECO:0000269|PubMed:18406324,
ECO:0000269|PubMed:2584148,
ECO:0000269|PubMed:893891}.
CROSSLNK 38 39 Thiazole-4-carboxylic acid (Ser-Cys).
{ECO:0000269|PubMed:18406324,
ECO:0000269|PubMed:2584148,
ECO:0000269|PubMed:893891}.
CROSSLNK 41 42 Thiazole-4-carboxylic acid (Thr-Cys).
{ECO:0000269|PubMed:18406324,
ECO:0000269|PubMed:2584148,
ECO:0000269|PubMed:893891}.
CROSSLNK 43 44 Thiazole-4-carboxylic acid (Glu-Cys).
{ECO:0000269|PubMed:18406324,
ECO:0000269|PubMed:2584148,
ECO:0000269|PubMed:893891}.
CROSSLNK 45 46 Thiazole-4-carboxylic acid (Cys-Cys).
{ECO:0000269|PubMed:18406324,
ECO:0000269|PubMed:2584148,
ECO:0000269|PubMed:893891}.
CROSSLNK 47 48 Thiazole-4-carboxylic acid (Ser-Cys).
{ECO:0000269|PubMed:18406324,
ECO:0000269|PubMed:2584148,
ECO:0000269|PubMed:893891}.
SEQUENCE 50 AA; 5364 MW; 7ADF5924AF2C7D00 CRC64;
MDAAHLSDLD IDALEISEFL DESRLEDSEV VAKVMSASCT TCECCCSCSS


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