JE-2147

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

MedKoo CAT#: 596203

CAS#: 186538-00-1

Description: JE-2147 belongs to the class of organic compounds known as hybrid peptides. These are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.


Chemical Structure

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JE-2147
CAS# 186538-00-1

Theoretical Analysis

MedKoo Cat#: 596203
Name: JE-2147
CAS#: 186538-00-1
Chemical Formula: C32H37N3O5S
Exact Mass: 575.2454
Molecular Weight: 575.72
Elemental Analysis: C, 66.76; H, 6.48; N, 7.30; O, 13.89; S, 5.57

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: JE-2147; AG1776; AG 1776; AG-1776; JE 2147; JE2147; KNI-764; KNI 764; KNI764;

IUPAC/Chemical Name: (R)-3-((2S,3S)-2-hydroxy-3-(3-hydroxy-2-methylbenzamido)-4-phenylbutanoyl)-5,5-dimethyl-N-(2-methylbenzyl)thiazolidine-4-carboxamide

InChi Key: CUFQBQOBLVLKRF-RZDMPUFOSA-N

InChi Code: InChI=1S/C32H37N3O5S/c1-20-11-8-9-14-23(20)18-33-30(39)28-32(3,4)41-19-35(28)31(40)27(37)25(17-22-12-6-5-7-13-22)34-29(38)24-15-10-16-26(36)21(24)2/h5-16,25,27-28,36-37H,17-19H2,1-4H3,(H,33,39)(H,34,38)/t25-,27-,28+/m0/s1

SMILES Code: O=C([C@H]1N(C([C@@H](O)[C@@H](NC(C2=CC=CC(O)=C2C)=O)CC3=CC=CC=C3)=O)CSC1(C)C)NCC4=CC=CC=C4C

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

Preparing Stock Solutions

The following data is based on the product molecular weight 575.72 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: Hidaka K, Kimura T, Abdel-Rahman HM, Nguyen JT, McDaniel KF, Kohlbrenner WE, Molla A, Adachi M, Tamada T, Kuroki R, Katsuki N, Tanaka Y, Matsumoto H, Wang J, Hayashi Y, Kempf DJ, Kiso Y. Small-sized human immunodeficiency virus type-1 protease inhibitors containing allophenylnorstatine to explore the S2' pocket. J Med Chem. 2009 Dec 10;52(23):7604-17. doi: 10.1021/jm9005115. PubMed PMID: 19954246.

2: Perryman AL, Lin JH, Andrew McCammon J. Optimization and computational evaluation of a series of potential active site inhibitors of the V82F/I84V drug-resistant mutant of HIV-1 protease: an application of the relaxed complex method of structure-based drug design. Chem Biol Drug Des. 2006 May;67(5):336-45. PubMed PMID: 16784458.

3: Bandyopadhyay P, Meher BR. Drug resistance of HIV-1 protease against JE-2147: I47V mutation investigated by molecular dynamics simulation. Chem Biol Drug Des. 2006 Feb;67(2):155-61. PubMed PMID: 16492163.

4: Randolph JT, DeGoey DA. Peptidomimetic inhibitors of HIV protease. Curr Top Med Chem. 2004;4(10):1079-95. Review. PubMed PMID: 15193140.

5: Mimoto T, Terashima K, Nojima S, Takaku H, Nakayama M, Shintani M, Yamaoka T, Hayashi H. Structure-activity and structure-metabolism relationships of HIV protease inhibitors containing the 3-hydroxy-2-methylbenzoyl-allophenylnorstatine structure. Bioorg Med Chem. 2004 Jan 2;12(1):281-93. PubMed PMID: 14697794.

6: Reiling KK, Endres NF, Dauber DS, Craik CS, Stroud RM. Anisotropic dynamics of the JE-2147-HIV protease complex: drug resistance and thermodynamic binding mode examined in a 1.09 A structure. Biochemistry. 2002 Apr 9;41(14):4582-94. PubMed PMID: 11926820.

7: Davis DA, Read-Connole E, Pearson K, Fales HM, Newcomb FM, Moskovitz J, Yarchoan R. Oxidative modifications of kynostatin-272, a potent human immunodeficiency virus type 1 protease inhibitor: potential mechanism for altered activity in monocytes/macrophages. Antimicrob Agents Chemother. 2002 Feb;46(2):402-8. PubMed PMID: 11796349; PubMed Central PMCID: PMC127045.

8: Gatanaga H, Suzuki Y, Tsang H, Yoshimura K, Kavlick MF, Nagashima K, Gorelick RJ, Mardy S, Tang C, Summers MF, Mitsuya H. Amino acid substitutions in Gag protein at non-cleavage sites are indispensable for the development of a high multitude of HIV-1 resistance against protease inhibitors. J Biol Chem. 2002 Feb 22;277(8):5952-61. Epub 2001 Dec 10. PubMed PMID: 11741936.

9: Yoshimura K, Kato R, Yusa K, Kavlick MF, Maroun V, Nguyen A, Mimoto T, Ueno T, Shintani M, Falloon J, Masur H, Hayashi H, Erickson J, Mitsuya H. JE-2147: a dipeptide protease inhibitor (PI) that potently inhibits multi-PI-resistant HIV-1. Proc Natl Acad Sci U S A. 1999 Jul 20;96(15):8675-80. PubMed PMID: 10411934; PubMed Central PMCID: PMC17575.

10: Mimoto T, Kato R, Takaku H, Nojima S, Terashima K, Misawa S, Fukazawa T, Ueno T, Sato H, Shintani M, Kiso Y, Hayashi H. Structure-activity relationship of small-sized HIV protease inhibitors containing allophenylnorstatine. J Med Chem. 1999 May 20;42(10):1789-802. PubMed PMID: 10346931.