CAS 1393-48-2

Thiostrepton

Description:

Thiostrepton is a naturally occurring thiopeptide antibiotic, primarily produced by the bacterium *Streptomyces azureus*. It is characterized by its complex structure, which includes a unique bicyclic core and multiple sulfur-containing moieties, contributing to its biological activity. Thiostrepton exhibits potent antimicrobial properties, particularly against Gram-positive bacteria, and has been studied for its potential applications in treating various infections. The compound functions by inhibiting protein synthesis, specifically targeting the ribosomal RNA, which disrupts the translation process in bacterial cells. In addition to its antibacterial effects, thiostrepton has shown promise in cancer research due to its ability to interfere with cellular signaling pathways. It is typically administered in a laboratory setting, and its use is primarily restricted to research purposes. Safety precautions are necessary when handling thiostrepton, as with many antibiotics, to prevent the development of resistance and ensure effective therapeutic outcomes. Overall, thiostrepton represents a significant compound in the field of microbiology and medicinal chemistry.

Formula: C₇₂H₈₅N₁₉O₁₈S₅

InChI: InChI=1S/C72H85N19O18S5/c1-14-26(3)47-63(105)78-30(7)57(99)75-28(5)56(98)76-31(8)58(100)91-72-19-18-40(66-85-43(22-111-66)59(101)77-29(6)55(97)74-27(4)54(73)96)81-52(72)42-21-112-67(83-42)49(34(11)109-69(107)41-20-37(32(9)92)36-16-17-39(79-47)51(95)50(36)80-41)89-60(102)44-24-113-68(86-44)53(71(13,108)35(12)94)90-62(104)45-23-110-65(84-45)38(15-2)82-64(106)48(33(10)93)88-61(103)46-25-114-70(72)87-46/h15-17,20-22,24-26,30-35,39,45,47-49,51-53,79,92-95,108H,4-6,14,18-19,23H2,1-3,7-13H3,(H2,73,96)(H,74,97)(H,75,99)(H,76,98)(H,77,101)(H,78,105)(H,82,106)(H,88,103)(H,89,102)(H,90,104)(H,91,100)/b38-15-/t26-,30-,31-,32-,33+,34+,35+,39+,45+,47-,48-,49-,51-,52+,53+,71+,72+/m0/s1

InChI key: InChIKey=NSFFHOGKXHRQEW-AIHSUZKVSA-N

SMILES: O=C1N[C@]23[C@@](C=4N=C(SC4)[C@@](NC(=O)C=5N=C(SC5)[C@]([C@]([C@@H](C)O)(C)O)(NC(=O)[C@@]6(N=C(\C(=C\C)\NC(=O)[C@]([C@@H](C)O)(NC(=O)C=7N=C2SC7)[H])SC6)[H])[H])([C@@H](C)OC(=O)C=8N=C9C(=C([C@H](C)O)C8)C=C[C@]([C@@H]9O)(N[C@@]([C@H](CC)C)(C(=O)N[C@@H](C)C(=O)NC(=C)C(=O)N[C@H]1C)[H])[H])[H])(N=C(CC3)C%10=NC(C(NC(C(NC(C(N)=O)=C)=O)=C)=O)=CS%10)[H]

Synonyms:

• Alaninamide, <span class="text-smallcaps">L</smallcap>-threonyl-(4S)-2-[(1Z)-1-amino-1-propenyl]-4,5-dihydro-4-thiazolecarbonyl-2-[(1S,2S,3R)-1-amino-2,3-dihydroxy-2-methylbutyl]-4-thiazolecarbonyl-2-[(5R,6S)-6-[2-[(1S,2R)-1-amino-2-hydroxypropyl]-4-thiazolyl]-5-[[N-[(7R,8S)-2-carboxy-7,8-dihydro-8-hydroxy-4-[(1S)-1-hydroxyethyl]-7-quinolinyl]-<smallcap>L</smallcap>-isoleucyl-<smallcap>L</smallcap>-alanyl-2,3-didehydroalanyl-<smallcap>L</span>-alanyl]amino]-5-(4-carboxy-2-thiazolyl)-3,4,5,6-tetrahydro-2-pyridinyl]-4-thiazolecarbonyl-2,3-didehydroalanyl-2,3-didehydro-, (1′→4)-lactone, (4→1)-lactam
• Alaninamide, N-[(7R,8S)-2-carboxy-7,8-dihydro-8-hydroxy-4-[(1S)-1-hydroxyethyl]-7-quinolinyl]-<span class="text-smallcaps">L</smallcap>-isoleucyl-<smallcap>L</smallcap>-alanyl-2,3-didehydroalanyl-<smallcap>L</span>-alanyl-2-[(4aR,11S,14Z,18S,21S,28S,32aS)-4a-amino-21-[(1S,2R)-1,2-dihydroxy-1-methylpropyl]-14-ethylidene-3,4,4a,9,10,11,12,13,14,18,19,20,21,27,28,32a-hexadecahydro-11,28-bis[(1R)-1-hydroxyethyl]-9,12,19,26-tetraoxo-17H,26H-8,5:18,15:25,22:32,29-tetranitrilo-5H,15H-pyrido[3,2-m][1,11,17,24,4,7,20,27]tetrathiatetraazacyclotriacontin-2-yl]-4-thiazolecarbonyl-2,3-didehydroalanyl-2,3-didehydro-, (1→5²⁸)-lactone
• Bryamycin
• Gargon
• N-{3-[(3-amino-3-oxoprop-1-en-2-yl)amino]-3-oxoprop-1-en-2-yl}-2-[(11E)-37-(butan-2-yl)-18-(2,3-dihydroxybutan-2-yl)-11-ethylidene-59-hydroxy-8,31-bis(1-hydroxyethyl)-26,40,46-trimethyl-43-methylidene-6,9,16,23,28,38,41,44,47-nonaoxo-27-oxa-3,13,20,56-tetrathia-7,10,17,24,36,39,42,45,48,52,58,61,62,63,64-pentadecaazanonacyclo[23.23.9.3~29,35~.1~2,5~.1~12,15~.1~19,22~.1~54,57~.0~1,53~.0~32,60~]tetrahexaconta-2(64),4,12(63),19(62),21,29,31,33,51,54,57,60-dodecaen-51-yl]-1,3-thiazole-4-carboxamide (non-preferred name)
• NSC 170365
• NSC 81722
• Thiactin
• Thiostrepton
• Thiostrepton A
• Alaninamide, N-[(7R,8S)-2-carboxy-7,8-dihydro-8-hydroxy-4-[(1S)-1-hydroxyethyl]-7-quinolinyl]-L-isoleucyl-L-alanyl-2,3-didehydroalanyl-L-alanyl-2-[(4aR,11S,14Z,18S,21S,28S,32aS)-4a-amino-21-[(1S,2R)-1,2-dihydroxy-1-methylpropyl]-14-ethylidene-3,4,4a,9,10,11,12,13,14,18,19,20,21,27,28,32a-hexadecahydro-11,28-bis[(1R)-1-hydroxyethyl]-9,12,19,26-tetraoxo-17H,26H-8,5:18,15:25,22:32,29-tetranitrilo-5H,15H-pyrido[3,2-m][1,11,17,24,4,7,20,27]tetrathiatetraazacyclotriacontin-2-yl]-4-thiazolecarbonyl-2,3-didehydroalanyl-2,3-didehydro-, (1→528)-lactone

Thiostrepton, Streptomyces laurentii, 90+%

CAS: 1393-48-2

Natural cyclic oligopeptide antibiotic

Formula: C₇₂H₈₅O₁₈N₁₉S₅

Purity: 90+%

Color and Shape: Powder

Molecular weight: 1664.89

Ref: 02-J62332

Thiostrepton

CAS: 1393-48-2

Antibiotics nesoi

Formula: C₇₂H₈₅N₁₉O₁₈S₅

Color and Shape: White Powder

Molecular weight: 1664.89

Ref: 45-1663700

Thiostrepton

CAS: 1393-48-2

Formula: C₇₂H₈₅N₁₉O₁₈S₅

Purity: 98%

Color and Shape: Solid

Molecular weight: 1664.8868

Ref: IN-DA006XMY

Thiostrepton from Streptomyces azureus

CAS: 1393-48-2

Thiostrepton from Streptomyces azureus

Formula: C₇₂H₈₅N₁₉O₁₈S₅

Purity: By hplc: 98.42% (Typical Value in Batch COA)

Color and Shape: white powder

Molecular weight: 1,664.89g/mol

Ref: 54-BIT1003

Thiostrepton

CAS: 1393-48-2

Formula: C₇₂H₈₅O₁₈N₁₉S₅

Purity: ≥ 98.0%

Color and Shape: White to pale yellow powder

Molecular weight: 1664.89

Ref: 7W-GA3924

Thiostrepton

CAS: 1393-48-2

Thiostrepton is a cyclic peptide from Streptomyces, active against gram-positive bacteria, used in veterinary medicine for mastitis and skin issues.

Formula: C₇₂H₈₅N₁₉O₁₈S₅

Purity: 98.09% - 99.57%

Color and Shape: Solid

Molecular weight: 1664.89

Ref: TM-T1679

Thiostrepton

Controlled Product

CAS: 1393-48-2

Stability Hygroscopic
Applications Natural antibiotic derived from Streptomyces.
References Starosta, A., et al.; Chem. Biol., 16, 1087 (2009), Gohil, V., et al.: Nat. Biotechnol., 28, 249 (2010), Kwok, J., et al.: Mol. Cancer Res., 8, 24 (2010),

Formula: C₇₂H₈₅N₁₉O₁₈S₅

Color and Shape: Neat

Molecular weight: 1664.89

Ref: TR-T375150

Thiostrepton

CAS: 1393-48-2

Thiostrepton is a thiopeptide antibiotic with action on bacterial protein synthesis by binding to the ribosome and is used for treating bacterial infections in veterinary medicine and research applications.

Formula: C₇₂H₈₅N₁₉O₁₈S₅

Purity: Min. 95%

Color and Shape: White To Light (Or Pale) Yellow Solid

Molecular weight: 1,664.89 g/mol

Ref: 3D-FT28240