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| ] 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 | ] 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''' 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> | | 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> | ||
Revision as of 18:44, 28 July 2007
Gramicidin S is a derivative of gramicidin, produced by the Gram positive bacterium Bacillus brevis var. G.-B. 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. 1,300 and is a transparent yellow or light yellow liquid and is usually encapsulated in two-percent sterile spirit solution. First used in 1943 by 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
- "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) -
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)
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