N-Carbethoxyhistidine

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MedKoo CAT#: 597330

CAS#: 27932-76-9

Description: N-Carbethoxyhistidine is used to protect amine functional groups.


Price and Availability

Size Price Shipping out time Quantity
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Pricing updated 2020-08-08. Prices are subject to change without notice.

N-Carbethoxyhistidine is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 597330
Name: N-Carbethoxyhistidine
CAS#: 27932-76-9
Chemical Formula: C9H13N3O4
Exact Mass: 227.0906
Molecular Weight: 227.22
Elemental Analysis: C, 47.57; H, 5.77; N, 18.49; O, 28.16


Synonym: N-Carbethoxyhistidine;

IUPAC/Chemical Name: (ethoxycarbonyl)-L-histidine

InChi Key: XSDVNQZWTFDETM-ZETCQYMHSA-N

InChi Code: InChI=1S/C9H13N3O4/c1-2-16-9(15)12-7(8(13)14)3-6-4-10-5-11-6/h4-5,7H,2-3H2,1H3,(H,10,11)(H,12,15)(H,13,14)/t7-/m0/s1

SMILES Code: O=C(O)[C@H](CC1=CNC=N1)NC(OCC)=O


Technical Data

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


References

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2: Parker AR. Binding of the human "electron transferring flavoprotein" (ETF) to the medium chain acyl-CoA dehydrogenase (MCAD) involves an arginine and histidine residue. J Enzyme Inhib Med Chem. 2003 Oct;18(5):453-62. PubMed PMID: 14692513.

3: Kaulpiboon J, Pongsawasdi P. Identification of essential histidines in cyclodextrin glycosyltransferase isoform 1 from Paenibacillus sp. A11. J Biochem Mol Biol. 2003 Jul 31;36(4):409-16. PubMed PMID: 12895301.

4: Weng LX, Xu JL, Li Q, Birch RG, Zhang LH. Identification of the essential histidine residue for high-affinity binding of AlbA protein to albicidin antibiotics. Microbiology. 2003 Feb;149(Pt 2):451-7. PubMed PMID: 12624207.

5: Mazumdar A, Bandyopadhyay D, Bandyopadhyay U, Banerjee RK. Probing the role of active site histidine residues in the catalytic activity of lacrimal gland peroxidase. Mol Cell Biochem. 2002 Aug;237(1-2):21-30. PubMed PMID: 12236583.

6: Hsiao YY, Van RC, Hung HH, Pan RL. Diethylpyrocarbonate inhibition of vacuolar H+-pyrophosphatase possibly involves a histidine residue. J Protein Chem. 2002 Jan;21(1):51-8. PubMed PMID: 11902667.

7: Chu CL, Hsiao YY, Chen CH, Van RC, Lin WJ, Pan RL. Inhibition of plant vacuolar H(+)-ATPase by diethylpyrocarbonate. Biochim Biophys Acta. 2001 Jul 2;1506(1):12-22. PubMed PMID: 11418093.

8: Bhattacharyya DK, Kwon O, Meganathan R. Vitamin K2 (menaquinone) biosynthesis in Escherichia coli: evidence for the presence of an essential histidine residue in o-succinylbenzoyl coenzyme A synthetase. J Bacteriol. 1997 Oct;179(19):6061-5. PubMed PMID: 9324253; PubMed Central PMCID: PMC179509.

9: Wakayama M, Tsutsumi T, Yada H, Sakai K, Moriguchi M. Chemical modification of histidine residue of N-acyl-D-Glutamate amidohydrolase from Pseudomonas sp. 5f-1. Biosci Biotechnol Biochem. 1996 Apr;60(4):650-3. PubMed PMID: 8829533.

10: Rúa J, Soler J, Busto F, de Arriaga D. The pH dependence and modification by diethyl pyrocarbonate of isocitrate lyase from Phycomyces blakesleeanus. Eur J Biochem. 1995 Sep 1;232(2):381-90. PubMed PMID: 7556185.

11: Imamura Y, Higuchi T, Otagiri M. Chemical modification of histidine residue in substrate-binding domain of carbonyl reductase from rabbit kidney. Biochem Mol Biol Int. 1993 Dec;31(6):1105-10. PubMed PMID: 8193594.

12: Bhattacharyya DK, Bandyopadhyay U, Banerjee RK. Chemical and kinetic evidence for an essential histidine residue in the electron transfer from aromatic donor to horseradish peroxidase compound I. J Biol Chem. 1993 Oct 25;268(30):22292-8. PubMed PMID: 8226738.

13: Tokuda H, Yamanaka M, Mizushima S. Histidine residues are involved in translocation-coupled ATP hydrolysis by the Sec-A protein. Biochem Biophys Res Commun. 1993 Sep 30;195(3):1415-21. PubMed PMID: 8216277.

14: Li C, Moore DS, Rosenberg RC. Circular dichroism studies of diethyl pyrocarbonate-modified histidine in hen egg white lysozyme. J Biol Chem. 1993 May 25;268(15):11090-6. PubMed PMID: 8496171.

15: Bhattacharyya DK, Bandyopadhyay U, Banerjee RK. Chemical and kinetic evidence for an essential histidine in horseradish peroxidase for iodide oxidation. J Biol Chem. 1992 May 15;267(14):9800-4. PubMed PMID: 1577815.

16: Nakayama T, Tanabe H, Deyashiki Y, Shinoda M, Hara A, Sawada H. Chemical modification of cysteinyl, lysyl and histidyl residues of mouse liver 17 beta-hydroxysteroid dehydrogenase. Biochim Biophys Acta. 1992 Apr 8;1120(2):144-50. PubMed PMID: 1562580.

17: Badet-Denisot MA, Badet B. Chemical modification of glucosamine-6-phosphate synthase by diethyl pyrocarbonate: evidence of histidine requirement for enzymatic activity. Arch Biochem Biophys. 1992 Feb 1;292(2):475-8. PubMed PMID: 1731613.

18: Kim YS, Kim YI, Bang SK. Chemical modification of Pseudomonas fluorescens malonyl-CoA synthetase by diethylpyrocarbonate: kinetic evidence for an essential histidyl residue on alpha subunit. J Protein Chem. 1991 Aug;10(4):407-13. PubMed PMID: 1781886.

19: Morjana NA, Scarborough GA. Evidence for an essential histidine residue in the Neurospora crassa plasma membrane H+-ATPase. Biochim Biophys Acta. 1989 Oct 2;985(1):19-25. PubMed PMID: 2528992.

20: Gacheru SN, Trackman PC, Kagan HM. Evidence for a functional role for histidine in lysyl oxidase catalysis. J Biol Chem. 1988 Nov 15;263(32):16704-8. PubMed PMID: 2903154.