Tryptophanamide

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

MedKoo CAT#: 598012

CAS#: 20696-57-5

Description: Tryptophanamide is used as inhibitor of chymotrypsin.


Chemical Structure

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Tryptophanamide
CAS# 20696-57-5

Theoretical Analysis

MedKoo Cat#: 598012
Name: Tryptophanamide
CAS#: 20696-57-5
Chemical Formula: C11H13N3O
Exact Mass: 203.11
Molecular Weight: 203.240
Elemental Analysis: C, 65.01; H, 6.45; N, 20.68; O, 7.87

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Tryptophanamide; S-Tryptophanamide;

IUPAC/Chemical Name: (S)-2-amino-3-(1H-indol-3-yl)propanamide

InChi Key: JLSKPBDKNIXMBS-VIFPVBQESA-N

InChi Code: InChI=1S/C11H13N3O/c12-9(11(13)15)5-7-6-14-10-4-2-1-3-8(7)10/h1-4,6,9,14H,5,12H2,(H2,13,15)/t9-/m0/s1

SMILES Code: O=C(N)[C@@H](N)CC1=CNC2=C1C=CC=C2

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 203.24 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Shou M, Terashima H, Aizawa S, Taga A, Yamamoto A, Kodama S. Simultaneous Enantioseparation of Aldohexoses and Aldopentoses Derivatized With L-Tryptophanamide by Reversed Phase HPLC Using Butylboronic Acid as a Complexation Reagent of Monosaccharides. Chirality. 2015 Jul;27(7):417-21. doi: 10.1002/chir.22456. Epub 2015 May 20. PubMed PMID: 25994510.

2: Kowalska-Baron A, Gałęcki K, Wysocki S. Temperature study of indole, tryptophan and N-acetyl-L-tryptophanamide (NATA) triplet-state quenching by iodide in aqueous solution. Spectrochim Acta A Mol Biomol Spectrosc. 2013 Jul;111:42-8. doi: 10.1016/j.saa.2013.03.086. Epub 2013 Mar 29. PubMed PMID: 23602958.

3: BERNHARD RA, NIEMANN C. A DILATOMETRIC INVESTIGATION OF THE ALPHA-CHYMOTRYPSIN-CATALYZED HYDROLYSIS OF NICOTINYL-L-TRYPTOPHANAMIDE. Arch Biochem Biophys. 1965 Apr;110:195-9. PubMed PMID: 14321852.

4: Andrews D, Trezeguet V, Merle M, Graves PV, Muench KH, Labouesse B. Tryptophanamide formation by Escherichia coli tryptophanyl-tRNA synthetase. Eur J Biochem. 1985 Jan 2;146(1):201-9. PubMed PMID: 3881255.

5: Cardenas AE, Jas GS, DeLeon KY, Hegefeld WA, Kuczera K, Elber R. Unassisted transport of N-acetyl-L-tryptophanamide through membrane: experiment and simulation of kinetics. J Phys Chem B. 2012 Mar 8;116(9):2739-50. doi: 10.1021/jp2102447. Epub 2012 Feb 22. PubMed PMID: 22313494; PubMed Central PMCID: PMC3302722.

6: Kowalska-Baron A, Chan M, Gałęcki K, Wysocki S. Photophysics of indole, tryptophan and N-acetyl-L-tryptophanamide (NATA): heavy atom effect. Spectrochim Acta A Mol Biomol Spectrosc. 2012 Dec;98:282-9. doi: 10.1016/j.saa.2012.08.017. Epub 2012 Aug 19. PubMed PMID: 22964241.

7: Karle IL. Comparison of stereospecific conformations for threo and erythro beta-hydroxy-N-acetyl-tryptophanamide. Int J Pept Protein Res. 1980 Nov;16(5):471-6. PubMed PMID: 7216622.

8: O'Leary MH, Kluetz MD. Identification of the rate-limiting step in the chymotrypsin-catalyzed hydrolysis of N-acetyl-L-tryptophanamide. J Am Chem Soc. 1970 Oct 7;92(20):6089-90. PubMed PMID: 5459201.

9: Davis DM, McLoskey D, Birch DJ, Gellert PR, Kittlety RS, Swart RM. The fluorescence and circular dichroism of proteins in reverse micelles: application to the photophysics of human serum albumin and N-acetyl-L-tryptophanamide. Biophys Chem. 1996 Jun 11;60(3):63-77. PubMed PMID: 8679927.

10: Himoe A, Parks PC, Hess GP. Investigations of the chymotrypsin-catalyzed hydrolysis of specific substrates. I. The pH dependence of the catalytic hydrolysis of N-acetyl-L-tryptophanamide by three forms of the enzyme at alkaline pH. J Biol Chem. 1967 Mar 10;242(5):919-29. PubMed PMID: 6020443.

11: Zelent B, Kuśba J, Gryczynski I, Johnson ML, Lakowicz JR. Time-resolved and steady-state fluorescence quenching of N-acetyl-L-tryptophanamide by acrylamide and iodide. Biophys Chem. 1998 Jul 13;73(1-2):53-75. PubMed PMID: 9697300.

12: Zelent B, Kuśba J, Gryczynski I, Johnson ML, Lakowicz JR. Distance-dependent fluorescence quenching ofN-acetyl-L-tryptophanamide by acrylamide. J Fluoresc. 1993 Sep;3(3):199-207. doi: 10.1007/BF00862743. PubMed PMID: 24234834.

13: O'Leary MH, Kluetz MD. Nitrogen isotope effects on the chymotrypsin-catalyzed hydrolysis of N-acetyl-L-tryptophanamide. J Am Chem Soc. 1972 May 17;94(10):3585-9. PubMed PMID: 5032959.

14: Gryczynski I, Malicka J, Lukomska J, Gryczynski Z, Lakowicz JR. Surface plasmon-coupled polarized emission of N-acetyl-l-tryptophanamide. Photochem Photobiol. 2004 Nov-Dec;80(3):482-5. PubMed PMID: 15623334.

15: Reddi E, Lambert CR, Jori G, Rodgers MA. Photokinetic and photophysical measurements of the sensitized photooxidation of the tryptophyl residue in N-acetyl tryptophanamide and in human serum albumin. Photochem Photobiol. 1987 Mar;45(3):345-51. PubMed PMID: 3562591.

16: Ruan K, Tian S, Lange R, Balny C. Pressure effects on tryptophan and its derivatives. Biochem Biophys Res Commun. 2000 Mar 24;269(3):681-6. PubMed PMID: 10720476.

17: El Guerdaoui A, Tijar R, El Merbouh B, Bourjila M, El Bouzaidi RD, El Gridani A. A comprehensive conformational space analysis of N-formyl-l-tryptophanamide system by using a genetic algorithm for multi-modal search. J Mol Graph Model. 2017 Aug;75:137-148. doi: 10.1016/j.jmgm.2017.05.008. Epub 2017 May 18. PubMed PMID: 28575796.

18: Silver MS, James SL. Surprising consequences of the tendency of pepsin to catalyze condensation reactions between small peptides. Biochim Biophys Acta. 1983 Feb 28;743(1):13-22. PubMed PMID: 6402022.

19: Stepp LR, Novakoski MA. Effect of 5-hydroxytryptamine on sodium- and potassium-dependent adenosine triphosphatase and its reactivity toward ouabain. Arch Biochem Biophys. 1997 Jan 1;337(1):43-53. PubMed PMID: 8990266.

20: Lee BL, Kuczera K, Middaugh CR, Jas GS. Permeation of the three aromatic dipeptides through lipid bilayers: Experimental and computational study. J Chem Phys. 2016 Jun 28;144(24):245103. doi: 10.1063/1.4954241. PubMed PMID: 27369545.