Cyclotheonamide A | CAS#129033-04-1 | cyclic peptide

MedKoo Cat#: 597753 | Name: Cyclotheonamide A

Description:

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

Cyclotheonamide A is a cyclic peptide isolated from the marine sponge Theonella.

Chemical Structure

Cyclotheonamide A

CAS#129033-04-1

Theoretical Analysis

MedKoo Cat#: 597753

Name: Cyclotheonamide A

CAS#: 129033-04-1

Chemical Formula: C36H45N9O8

Exact Mass: 731.3391

Molecular Weight: 731.81

Elemental Analysis: C, 59.09; H, 6.20; N, 17.23; O, 17.49

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

Cyclotheonamide A;

IUPAC/Chemical Name

N-((3S,7R,10S,16S,21aS,E)-7-benzyl-3-(3-guanidinopropyl)-10-(4-hydroxybenzyl)-1,4,5,8,13,17-hexaoxo-2,3,4,5,6,7,8,9,10,13,14,15,16,17,19,20,21,21a-octadecahydro-1H-pyrrolo[2,1-j][1,4,8,11,15]pentaazacyclononadecin-16-yl)formamide

InChi Key

CDWXSPKJKIUEQF-BIXWYCRZSA-N

InChi Code

InChI=1S/C36H45N9O8/c37-36(38)39-16-4-8-26-31(49)34(52)44-27(19-22-6-2-1-3-7-22)32(50)42-24(18-23-10-13-25(47)14-11-23)12-15-30(48)40-20-28(41-21-46)35(53)45-17-5-9-29(45)33(51)43-26/h1-3,6-7,10-15,21,24,26-29,47H,4-5,8-9,16-20H2,(H,40,48)(H,41,46)(H,42,50)(H,43,51)(H,44,52)(H4,37,38,39)/b15-12+/t24-,26+,27-,28+,29+/m1/s1

SMILES Code

O=C(N[C@@H](Cc1ccc(O)cc1)/C=C/C(NC[C@H](NC=O)C(N2CCC[C@H]2C(N[C@@H](CCCNC(N)=N)C(C(N3)=O)=O)=O)=O)=O)[C@H]3Cc4ccccc4

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

>3 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

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 731.81 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.

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: Maryanoff BE, Qiu X, Padmanabhan KP, Tulinsky A, Almond HR Jr, Andrade-Gordon P, Greco MN, Kauffman JA, Nicolaou KC, Liu A, et al. Molecular basis for the inhibition of human alpha-thrombin by the macrocyclic peptide cyclotheonamide A. Proc Natl Acad Sci U S A. 1993 Sep 1;90(17):8048-52. PubMed PMID: 8367461; PubMed Central PMCID: PMC47285. 2: Ganesh V, Lee AY, Clardy J, Tulinsky A. Comparison of the structures of the cyclotheonamide A complexes of human alpha-thrombin and bovine beta-trypsin. Protein Sci. 1996 May;5(5):825-35. PubMed PMID: 8732754; PubMed Central PMCID: PMC2143408. 3: Lewis SD, Ng AS, Baldwin JJ, Fusetani N, Naylor AM, Shafer JA. Inhibition of thrombin and other trypsin-like serine proteinases by cyclotheonamide A. Thromb Res. 1993 Apr 15;70(2):173-90. PubMed PMID: 8322286. 4: Schaschke N, Sommerhoff CP. Upgrading a natural product: inhibition of human beta-tryptase by cyclotheonamide analogues. ChemMedChem. 2010 Mar 1;5(3):367-70. doi: 10.1002/cmdc.200900484. PubMed PMID: 20077463. 5: Owens TD, Semple JE. Atom-economical synthesis of the N(10)-C(17) fragment of cyclotheonamides via a novel Passerini reaction-deprotection-acyl migration strategy. Org Lett. 2001 Oct 18;3(21):3301-4. PubMed PMID: 11594819. 6: Yli-Kauhaluoma J, Janda KD. Twisted alpha-keto amides as transition-state analogues for acyl-transfer reactions: synthesis of the immunoconjugates. Bioorg Med Chem. 1994 Jun;2(6):521-8. PubMed PMID: 7528089.