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MedKoo Cat#: 571477 | Name: Cispentacin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Cispentacin is a β-amino acid. It is naturally occurring and acts as a water-soluble antifungal antibiotic. It is effective against Candida.

Chemical Structure

Cispentacin
Cispentacin
CAS#3814-46-8

Theoretical Analysis

MedKoo Cat#: 571477

Name: Cispentacin

CAS#: 3814-46-8

Chemical Formula: C6H11NO2

Exact Mass: 129.0790

Molecular Weight: 129.16

Elemental Analysis: C, 55.80; H, 8.58; N, 10.84; O, 24.77

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Cispentacin
IUPAC/Chemical Name
Cyclopentanecarboxylic acid, 2-amino-
InChi Key
JWYOAMOZLZXDER-UHFFFAOYSA-N
InChi Code
InChI=1S/C6H11NO2/c7-5-3-1-2-4(5)6(8)9/h4-5H,1-3,7H2,(H,8,9)
SMILES Code
O=C(C1C(N)CCC1)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
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 129.16 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
1: Nonn M, Kiss L, Hänninen MM, Sillanpää R, Fülöp F. Synthesis of highly functionalized fluorinated cispentacin derivatives. Chem Biodivers. 2012 Nov;9(11):2571-81. doi: 10.1002/cbdv.201200323. PubMed PMID: 23161635. 2: Bunnage ME, Davies SG, Parkin RM, Roberts PM, Smith AD, Withey JM. Kinetic resolution of tert-butyl (RS)-3-alkylcyclopentene-1-carboxylates for the synthesis of homochiral 3-alkyl-cispentacin and 3-alkyl-transpentacin derivatives. Org Biomol Chem. 2004 Nov 21;2(22):3337-54. Epub 2004 Oct 20. PubMed PMID: 15534712. 3: Konishi M, Nishio M, Saitoh K, Miyaki T, Oki T, Kawaguchi H. Cispentacin, a new antifungal antibiotic. I. Production, isolation, physico-chemical properties and structure. J Antibiot (Tokyo). 1989 Dec;42(12):1749-55. PubMed PMID: 2516082. 4: Capobianco JO, Zakula D, Coen ML, Goldman RC. Anti-Candida activity of cispentacin: the active transport by amino acid permeases and possible mechanisms of action. Biochem Biophys Res Commun. 1993 Feb 15;190(3):1037-44. PubMed PMID: 8439305. 5: Aye Y, Davies SG, Garner AC, Roberts PM, Smith AD, Thomson JE. Parallel kinetic resolution of tert-butyl (RS)-3-oxy-substituted cyclopent-1-ene-carboxylates for the asymmetric synthesis of 3-oxy-substituted cispentacin and transpentacin derivatives. Org Biomol Chem. 2008 Jun 21;6(12):2195-203. doi: 10.1039/b802428f. Epub 2008 Apr 21. PubMed PMID: 18528582. 6: Langer O, Kählig H, Zierler-Gould K, Bats JW, Mulzer J. A bicyclic cispentacin derivative as a novel reverse turn inducer in a GnRH mimetic. J Org Chem. 2002 Oct 4;67(20):6878-83. PubMed PMID: 12353977. 7: Oki T, Hirano M, Tomatsu K, Numata K, Kamei H. Cispentacin, a new antifungal antibiotic. II. In vitro and in vivo antifungal activities. J Antibiot (Tokyo). 1989 Dec;42(12):1756-62. PubMed PMID: 2621158. 8: Davies SG, Garner AC, Long MJ, Smith AD, Sweet MJ, Withey JM. Parallel kinetic resolution of tert-butyl (RS)-3-alkyl-cyclopentene-1-carboxylates for the asymmetric synthesis of 3-alkyl-cispentacin derivatives. Org Biomol Chem. 2004 Nov 21;2(22):3355-62. Epub 2004 Oct 20. PubMed PMID: 15534713. 9: Davies SG, Sheppard RL, Smith AD, Thomson JE. Highly enantioselective organocatalysis of the Hajos-Parrish-Eder-Sauer-Wiechert reaction by the beta-amino acid cispentacin. Chem Commun (Camb). 2005 Aug 14;(30):3802-4. Epub 2005 Jun 30. PubMed PMID: 16041422. 10: Kiss L, Cherepanova M, Forró E, Fülöp F. A new access route to functionalized cispentacins from norbornene β-amino acids. Chemistry. 2013 Feb 4;19(6):2102-7. doi: 10.1002/chem.201203183. Epub 2012 Dec 19. PubMed PMID: 23255222. 11: Aggarwal VK, Roseblade SJ, Barrell JK, Alexander R. Highly diastereoselective nitrone cycloaddition onto a chiral ketene equivalent: asymmetric synthesis of cispentacin. Org Lett. 2002 Apr 4;4(7):1227-9. PubMed PMID: 11922825. 12: Forró E. New gas chromatographic method for the enantioseparation of beta-amino acids by a rapid double derivatization technique. J Chromatogr A. 2009 Feb 6;1216(6):1025-9. doi: 10.1016/j.chroma.2008.12.040. Epub 2008 Dec 25. PubMed PMID: 19131071. 13: Jethwaney D, Höfer M, Khaware RK, Prasad R. Functional reconstitution of a purified proline permease from Candida albicans: interaction with the antifungal cispentacin. Microbiology. 1997 Feb;143 ( Pt 2):397-404. PubMed PMID: 9043117. 14: Zanol M, Hermann R, Bernareggi A, Borgonovi M, Taglietti E, Zerilli LF. HPLC method for the quantitation of cispentacin enantiomers in rat urine. Boll Chim Farm. 1995 Jul-Aug;134(7):390-3. PubMed PMID: 7546543. 15: Davies SG, Garner AC, Long MJ, Morrison RM, Roberts PM, Savory ED, Smith AD, Sweet MJ, Withey JM. Kinetic resolution and parallel kinetic resolution of methyl (+/-)-5-alkyl-cyclopentene-1-carboxylates for the asymmetric synthesis of 5-alkyl-cispentacin derivatives. Org Biomol Chem. 2005 Aug 7;3(15):2762-75. Epub 2005 Jun 30. PubMed PMID: 16032355. 16: Aggarwal VK, Roseblade S, Alexander R. The use of enantiomerically pure ketene dithioacetal bis(sulfoxides) in highly diastereoselective intramolecular nitrone cycloadditions. Application in the total synthesis of the beta-amino acid (-)-cispentacin and the first asymmetric synthesis of cis-(3R,4R)-4-amino-pyrrolidine-3-carboxylic acid. Org Biomol Chem. 2003 Feb 21;1(4):684-91. PubMed PMID: 12929455. 17: Ötvös SB, Mándity IM, Kiss L, Fülöp F. Alkyne-azide cycloadditions with copper powder in a high-pressure continuous-flow reactor: high-temperature conditions versus the role of additives. Chem Asian J. 2013 Apr;8(4):800-8. doi: 10.1002/asia.201201125. Epub 2013 Feb 12. PubMed PMID: 23404792. 18: Delto JC, Kobayashi T, Benson M, McKiernan J, Abate-Shen C. Preclinical analyses of intravesical chemotherapy for prevention of bladder cancer progression. Oncotarget. 2013 Feb;4(2):269-76. PubMed PMID: 23563166; PubMed Central PMCID: PMC3712572. 19: Gecse Z, Ilisz I, Nonn M, Grecsó N, Fülöp F, Agneeswari R, Hyun MH, Péter A. High-performance liquid chromatographic enantioseparation of isoxazoline-fused 2-aminocyclopentanecarboxylic acids on a chiral ligand-exchange stationary phase. J Sep Sci. 2013 Apr;36(8):1335-42. doi: 10.1002/jssc.201201061. Epub 2013 Mar 19. PubMed PMID: 23512817. 20: Vass E, Strijowski U, Wollschläger K, Mándity IM, Szilvágyi G, Jewgiński M, Gaus K, Royo S, Majer Z, Sewald N, Hollósi M. VCD studies on cyclic peptides assembled from L-α-amino acids and a trans-2-aminocyclopentane- or trans-2-aminocyclohexane carboxylic acid. J Pept Sci. 2010 Nov;16(11):613-20. doi: 10.1002/psc.1272. PubMed PMID: 20848613.