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{{drugbox
]
|IUPAC_name=Gramicidin S
⚫ ] groups on the ] as well as ] of select amide nitrogens to force cyclic conformation. <ref>{{citation | title =Stereochemistry of Protected Ornithine Side Chains of Gramicidin S Derivatives: X-ray Crystal Structure of the Bis-Boc-tetra-N-methyl Derivative of Gramicidin S |first = Keiichi Yamada, Masafumi Unno, Kyoko Kobayashi, Hiroyuki Oku, Hatsuo Yamamura, Shuki Araki, Hideyuki Matsumoto, Ryoichi Katakai, and Masao Kawai
|image=GramicidinS.png
⚫ | journal = J. Am. Chem. Soc.; | year = 2002; | issue = 124 |page = 12684 - 12688; | DOI = 10.1021/ja020307t }}</ref>]] '''Gramicidin S''' is a derivative of ], produced by the ] bacterium ''Bacillus brevis var. G.-B''. Gramicidin S is a ], constructed as two identical ]s joined head to tail, formally written as ''cyclo''(-]-]-]-D-]-]-)<sub>2</sub>. That is to say, it forms a ring structure composed of five different amino acids, each one used twice within the structure. Another interesting point is that it utilizes two amino acids uncommon in ]: ] as well as the unnatural ] of ]. It is synthesized by gramicidin S synthetase.<ref>
|CAS_number=9062-61-7
⚫ {{Citation | last = Brick | first = Peter | author-link = Peter Brike | title = Structural basis for the activation of phenylalanine in the non-ribosomal biosynthesis of gramicidin S | journal = The EMBO Journal | volume = 16 | pages = 4174-4183 | date = 1997 | year = 1997 | DOI = 10.1093/emboj/16.14.4174 }}</ref> Structurally, Gramicidin S differs from ], which is a linear ] and forms a beta helix in ]s. The exact mechanism by which Gramicidin S works is not well known.
|ATC_prefix=
|ATC_suffix=
|ATC_supplemental=
|PubChem=73357
|DrugBank=
|C=60 | H=92 | N=12 | O=10
|molecular_weight=1140.7059 g/mol
|bioavailability=
|protein_bound=
|metabolism=
|elimination_half-life=
|excretion=
|pregnancy_AU=<!-- A / B1 / B2 / B3 / C / D / X -->
|pregnancy_US=<!-- A / B / C / D / X -->
|pregnancy_category=
|legal_AU=<!-- Unscheduled / S2 / S4 / S8 -->
|legal_UK=<!-- GSL / P / POM / CD -->
|legal_US=<!-- OTC / Rx-only -->
|legal_status=
|routes_of_administration= Topical
}}
⚫ ] groups on the ] as well as ] of select amide nitrogens to force cyclic conformation.<ref>{{citation | title =Stereochemistry of Protected Ornithine Side Chains of Gramicidin S Derivatives: X-ray Crystal Structure of the Bis-Boc-tetra-N-methyl Derivative of Gramicidin S |first = Keiichi Yamada, Masafumi Unno, Kyoko Kobayashi, Hiroyuki Oku, Hatsuo Yamamura, Shuki Araki, Hideyuki Matsumoto, Ryoichi Katakai, and Masao Kawai
| journal = J. Am. Chem. Soc.; | year = 2002; | issue = 124 |page = 12684 - 12688; | DOI = 10.1021/ja020307t }}</ref>]]
⚫ '''Gramicidin S''' or '''Gramicidin Soviet'''<ref>Gause, G. F. & Brazhnikova, M. G. (1944). ''Nature'' (London), '''154''', 703.</ref> is a derivative of ], produced by the ] bacterium ''Bacillus brevis''. Gramicidin S is a ], constructed as two identical ]s joined head to tail, formally written as ''cyclo''(-]-]-]-D-]-]-)<sub>2</sub>. That is to say, it forms a ring structure composed of five different amino acids, each one used twice within the structure.<ref>


{{Citation | last=Llamas-Saiz | first = Antonio | title= Double-stranded helical twisted b-sheet channels in crystals of gramicidin S grown in the presence of trifluoroacetic and hydrochloric acids | journal = Acta Crystallographica Section D | volume = D63 | pages = 401-407 | year = 2007 | DOI = 10.1107/S0907444906056435}}
⚫ It has a ] of ca. 1,300 and is a transparent yellow or light yellow liquid and is usually encapsulated in two-percent sterile spirit solution. First used in 1943 by ] during ] (thus is also known as Gramicidin S). It also exists in the form of pills (Latin: ''tabulettae Gramicidini'') and paste (''pasta Gramicidini''). The last could be also used as a ], being introduced into vagina by the special syringe.{{Fact|date=July 2007}}

</ref>Another interesting point is that it utilizes two amino acids uncommon in ]: ] as well as the unnatural ] of ]. It is synthesized by gramicidin S synthetase.<ref>

⚫ {{Citation | last = Brick | first = Peter | author-link = Peter Brike | title = Structural basis for the activation of phenylalanine in the non-ribosomal biosynthesis of gramicidin S | journal = The EMBO Journal | volume = 16 | pages = 4174-4183 | date = 1997 | year = 1997 | DOI = 10.1093/emboj/16.14.4174 }}</ref>

Structurally, Gramicidin S differs from ], which is a linear ] and forms a beta helix in ]s. The exact mechanism by which Gramicidin S works is not well known.

⚫ It has a ] of ca. 1,140 and is a solid, usually encapsulated in two-percent sterile spirit solution. First used in 1943 by ] during ] (thus is also known as Gramicidin S). It also exists in the form of pills (Latin: ''tabulettae Gramicidini'') and paste (''pasta Gramicidini''). The last could be also used as a ], being introduced into vagina by the special syringe.{{Fact|date=July 2007}}
==References== ==References==
<references /> <references />
Acta Cryst. (2007). D63, 401-407

] ]


Revision as of 20:17, 28 July 2007

Pharmaceutical compound
Gramicidin S
Clinical data
Routes of
administration		Topical
Identifiers
IUPAC name
  • Gramicidin S
CAS Number
PubChem CID
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC60H92N12O10
Molar mass1140.7059 g/mol g·mol
File:GS.png
Crystal structure of modified Gramicidin S. Modification includes Boc groups on the ornithine as well as methylation of select amide nitrogens to force cyclic conformation.

Gramicidin S or Gramicidin Soviet is a derivative of gramicidin, produced by the Gram positive bacterium Bacillus brevis. Gramicidin S is a cyclodecapeptide, constructed as two identical pentapeptides joined head to tail, formally written as cyclo(-Val-Orn-Leu-D-Phe-Pro-)2. That is to say, it forms a ring structure composed of five different amino acids, each one used twice within the structure.Another interesting point is that it utilizes two amino acids uncommon in peptides: ornithine as well as the unnatural stereoisomer of phenylalanine. It is synthesized by gramicidin S synthetase.

Structurally, Gramicidin S differs from Gramicidin D, which is a linear peptide and forms a beta helix in cellular membranes. The exact mechanism by which Gramicidin S works is not well known.

It has a molecular mass of ca. 1,140 and is a solid, usually encapsulated in two-percent sterile spirit solution. First used in 1943 by USSR during World War II (thus is also known as Gramicidin S). It also exists in the form of pills (Latin: tabulettae Gramicidini) and paste (pasta Gramicidini). The last could be also used as a contraceptive, being introduced into vagina by the special syringe.

References

  1. "Stereochemistry of Protected Ornithine Side Chains of Gramicidin S Derivatives: X-ray Crystal Structure of the Bis-Boc-tetra-N-methyl Derivative of Gramicidin S", J. Am. Chem. Soc.; (124): 12684 - 12688;, 2002;, doi:10.1021/ja020307t {{citation}}: |first= missing |last= (help); Check date values in: |year= (help)CS1 maint: extra punctuation (link) CS1 maint: multiple names: authors list (link) CS1 maint: year (link)
  2. Gause, G. F. & Brazhnikova, M. G. (1944). Nature (London), 154, 703.
  3. Llamas-Saiz, Antonio (2007), "Double-stranded helical twisted b-sheet channels in crystals of gramicidin S grown in the presence of trifluoroacetic and hydrochloric acids", Acta Crystallographica Section D, D63: 401–407, doi:10.1107/S0907444906056435
  4. Brick, Peter (1997), "Structural basis for the activation of phenylalanine in the non-ribosomal biosynthesis of gramicidin S", The EMBO Journal, 16: 4174–4183, doi:10.1093/emboj/16.14.4174{{citation}}: CS1 maint: date and year (link)

Acta Cryst. (2007). D63, 401-407

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