Gramicdin A
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MedKoo CAT#: 333081

CAS#: 11029-61-1

Description: Gramicidin A is a peptide component of gramicidin, an antibiotic mixture originally isolated from B. brevis.


Chemical Structure

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Gramicdin A
CAS# 11029-61-1

Theoretical Analysis

MedKoo Cat#: 333081
Name: Gramicdin A
CAS#: 11029-61-1
Chemical Formula: C99H140N20O17
Exact Mass: 1881.0705
Molecular Weight: 1882.332
Elemental Analysis: C, 63.17; H, 7.50; N, 14.88; O, 14.45

Price and Availability

Size Price Availability Quantity
5.0mg USD 250.0 2 Weeks
10.0mg USD 450.0 2 Weeks
25.0mg USD 950.0 2 Weeks
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Synonym: Gramicdin A;

IUPAC/Chemical Name: (R)-2-((2S,5R,8S,11R,14S,17R,20S,26S)-2-((1H-indol-3-yl)methyl)-17-isobutyl-5,8,11,26-tetraisopropyl-14,20-dimethyl-4,7,10,13,16,19,22,27,28-nonaoxo-3,6,9,12,15,18,21,24,25-nonaazaoctacosanamido)-N-((5S,8R,11S,14R,17S)-5,11-bis((1H-indol-3-yl)methyl)-1-hydroxy-18-(1H-indol-3-yl)-8,14-diisobutyl-4,7,10,13,16-pentaoxo-3,6,9,12,15-pentaazaoctadecan-17-yl)-4-methylpentanamide

InChi Key: ZWCXYZRRTRDGQE-LUPIJMBPSA-N

InChi Code: InChI=1S/C99H140N20O17/c1-51(2)37-73(109-86(123)59(17)107-81(122)49-105-96(133)82(55(9)10)106-50-121)89(126)108-60(18)87(124)117-84(57(13)14)98(135)119-85(58(15)16)99(136)118-83(56(11)12)97(134)116-80(44-64-48-104-72-34-26-22-30-68(64)72)95(132)112-76(40-54(7)8)92(129)115-79(43-63-47-103-71-33-25-21-29-67(63)71)94(131)111-75(39-53(5)6)91(128)114-78(42-62-46-102-70-32-24-20-28-66(62)70)93(130)110-74(38-52(3)4)90(127)113-77(88(125)100-35-36-120)41-61-45-101-69-31-23-19-27-65(61)69/h19-34,45-48,50-60,73-80,82-85,101-104,120H,35-44,49H2,1-18H3,(H,100,125)(H,105,133)(H,106,121)(H,107,122)(H,108,126)(H,109,123)(H,110,130)(H,111,131)(H,112,132)(H,113,127)(H,114,128)(H,115,129)(H,116,134)(H,117,124)(H,118,136)(H,119,135)/t59-,60-,73+,74+,75+,76+,77-,78-,79-,80-,82-,83+,84+,85-/m0/s1

SMILES Code: [H]C(N[C@H](C(NCC(N[C@@H](C)C(N[C@@H](C(N[C@@H](C)C(N[C@@H](C(N[C@H](C(N[C@@H](C(N[C@@H](CC1=CNC2=C1C=CC=C2)C(N[C@@H](C(N[C@@H](CC3=CNC4=C3C=CC=C4)C(N[C@@H](C(N[C@@H](CC5=CNC6=C5C=CC=C6)C(N[C@@H](C(N[C@@H](CC7=CNC8=C7C=CC=C8)C(NCCO)=O)=O)CC(C)C)=O)=O)CC(C)C)=O)=O)CC(C)C)=O)=O)C(C)C)=O)C(C)C)=O)C(C)C)=O)=O)CC(C)C)=O)=O)=O)C(C)C)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 1882.332 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Kaman WE, Nazmi K, Voskamp-Visser AI, Bikker FJ. Gramicidin A is hydrolyzed by a d-stereospecific peptidase produced by Bacillus anthracis. Environ Microbiol Rep. 2022 Apr 10. doi: 10.1111/1758-2229.13069. Epub ahead of print. PMID: 35403341.

2: Buta A, Nazaruk E, Dziubak D, Szewczyk A, Bilewicz R. Properties of electrode-supported lipid cubic mesophase films with embedded gramicidin A: structure and ion-transport studies. Bioelectrochemistry. 2022 Apr;144:108042. doi: 10.1016/j.bioelechem.2021.108042. Epub 2021 Dec 14. PMID: 34942573.

3: Haoyang WW, Xiao Q, Ye Z, Fu Y, Zhang DW, Li J, Xiao L, Li ZT, Hou JL. Gramicidin A-based unimolecular channel: cancer cell-targeting behavior and ion transport-induced apoptosis. Chem Commun (Camb). 2021 Feb 2;57(9):1097-1100. doi: 10.1039/d0cc08073j. PMID: 33443269.

4: Abel S, Marchi M. Deciphering the Structure of the Gramicidin A Channel in the Presence of AOT Reverse Micelles in Pentane Using Molecular Dynamics Simulations. J Phys Chem B. 2020 Dec 31;124(52):11802-11818. doi: 10.1021/acs.jpcb.0c08902. Epub 2020 Dec 21. PMID: 33346653.

5: Tawfik H, Puza S, Seemann R, Fleury JB. Transport Properties of Gramicidin A Ion Channel in a Free-Standing Lipid Bilayer Filled With Oil Inclusions. Front Cell Dev Biol. 2020 Sep 4;8:531229. doi: 10.3389/fcell.2020.531229. PMID: 33015051; PMCID: PMC7498540.

6: Takada Y, Itoh H, Paudel A, Panthee S, Hamamoto H, Sekimizu K, Inoue M. Discovery of gramicidin A analogues with altered activities by multidimensional screening of a one-bead-one-compound library. Nat Commun. 2020 Oct 1;11(1):4935. doi: 10.1038/s41467-020-18711-2. PMID: 33004797; PMCID: PMC7531004.

7: Carillo KD, Lo CJ, Tzou DM, Lin YH, Fang ST, Huang SH, Chen YC. The Effect of Calcium and Halide Ions on the Gramicidin A Molecular State and Antimicrobial Activity. Int J Mol Sci. 2020 Aug 27;21(17):6177. doi: 10.3390/ijms21176177. PMID: 32867026; PMCID: PMC7503548.

8: Seibert J, Champagne B, Grimme S, de Wergifosse M. Dynamic Structural Effects on the Second-Harmonic Generation of Tryptophane-Rich Peptides and Gramicidin A. J Phys Chem B. 2020 Apr 2;124(13):2568-2578. doi: 10.1021/acs.jpcb.0c00643. Epub 2020 Mar 23. PMID: 32148035.

9: Mao J, Itoh H, Sakurai K, Inoue M. Phospholipid-Dependent Functions of a Macrocyclic Analogue of the Ion-Channel-Forming Antibiotic Gramicidin A. Chem Pharm Bull (Tokyo). 2020;68(2):173-178. doi: 10.1248/cpb.c19-00967. PMID: 32009085.

10: Nishio M, Teranishi Y, Morioka K, Yanagida A, Shoji A. Real-time assay for exosome membrane fusion with an artificial lipid membrane based on enhancement of gramicidin A channel conductance. Biosens Bioelectron. 2020 Feb 15;150:111918. doi: 10.1016/j.bios.2019.111918. Epub 2019 Nov 23. PMID: 31818753.

11: Roux B. Calculating the Effect of Membrane Thickness on the Lifetime of the Gramicidin A Channel: A Landmark. Biophys J. 2019 Nov 19;117(10):1779-1780. doi: 10.1016/j.bpj.2019.10.005. Epub 2019 Oct 10. PMID: 31668331; PMCID: PMC7019011.

12: Reiter R, Zaitseva E, Baaken G, Halimeh I, Behrends JC, Zumbuehl A. Activity of the Gramicidin A Ion Channel in a Lipid Membrane with Switchable Physical Properties. Langmuir. 2019 Nov 19;35(46):14959-14966. doi: 10.1021/acs.langmuir.9b02752. Epub 2019 Nov 7. PMID: 31645105.

13: Gambucci M, Gentili PL, Sassi P, Latterini L. A multi-spectroscopic approach to investigate the interactions between Gramicidin A and silver nanoparticles. Soft Matter. 2019 Aug 28;15(32):6571-6580. doi: 10.1039/c9sm01110b. Epub 2019 Jul 31. PMID: 31364666.

14: Wang RQ, Geng J, Sheng WJ, Liu XJ, Jiang M, Zhen YS. The ionophore antibiotic gramicidin A inhibits pancreatic cancer stem cells associated with CD47 down-regulation. Cancer Cell Int. 2019 May 22;19:145. doi: 10.1186/s12935-019-0862-6. PMID: 31139022; PMCID: PMC6532126.

15: Kondrashov OV, Galimzyanov TR, Pavlov KV, Kotova EA, Antonenko YN, Akimov SA. Membrane Elastic Deformations Modulate Gramicidin A Transbilayer Dimerization and Lateral Clustering. Biophys J. 2018 Aug 7;115(3):478-493. doi: 10.1016/j.bpj.2018.07.004. Epub 2018 Jul 11. PMID: 30049405; PMCID: PMC6084527.

16: Khailova LS, Rokitskaya TI, Kovalchuk SI, Kotova ЕА, Sorochkina AI, Antonenko YN. Role of mitochondrial outer membrane in the uncoupling activity of N-terminally glutamate-substituted gramicidin A. Biochim Biophys Acta Biomembr. 2019 Jan;1861(1):281-287. doi: 10.1016/j.bbamem.2018.06.013. Epub 2018 Jun 22. PMID: 29940153.

17: Kim YH, Hang L, Cifelli JL, Sept D, Mayer M, Yang J. Frequency-Based Analysis of Gramicidin A Nanopores Enabling Detection of Small Molecules with Picomolar Sensitivity. Anal Chem. 2018 Feb 6;90(3):1635-1642. doi: 10.1021/acs.analchem.7b02961. Epub 2018 Jan 16. PMID: 29266927.

18: Beaven AH, Sodt AJ, Pastor RW, Koeppe RE 2nd, Andersen OS, Im W. Characterizing Residue-Bilayer Interactions Using Gramicidin A as a Scaffold and Tryptophan Substitutions as Probes. J Chem Theory Comput. 2017 Oct 10;13(10):5054-5064. doi: 10.1021/acs.jctc.7b00400. Epub 2017 Sep 22. PMID: 28870079; PMCID: PMC5634937.

19: Sodt AJ, Beaven AH, Andersen OS, Im W, Pastor RW. Gramicidin A Channel Formation Induces Local Lipid Redistribution II: A 3D Continuum Elastic Model. Biophys J. 2017 Mar 28;112(6):1198-1213. doi: 10.1016/j.bpj.2017.01.035. PMID: 28355547; PMCID: PMC5376118.

20: Beaven AH, Maer AM, Sodt AJ, Rui H, Pastor RW, Andersen OS, Im W. Gramicidin A Channel Formation Induces Local Lipid Redistribution I: Experiment and Simulation. Biophys J. 2017 Mar 28;112(6):1185-1197. doi: 10.1016/j.bpj.2017.01.028. PMID: 28355546; PMCID: PMC5375002.