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MedKoo Cat#: 146280 | Name: Allysine

Description:

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

Allysine is a naturally occurring amino acid derivative formed by the oxidative deamination of lysine residues in collagen and elastin by the enzyme lysyl oxidase. It plays a crucial role in the cross-linking of collagen and elastin fibers, which is essential for the structural integrity and elasticity of connective tissues. While not used as a pesticide or pharmaceutical agent, allysine is significant in biomedical research, particularly in studies related to tissue repair, fibrosis, and aging. Its mechanism involves forming covalent cross-links that stabilize the extracellular matrix and contribute to tissue strength and resilience.

Chemical Structure

Allysine
Allysine
CAS#6665-12-9

Theoretical Analysis

MedKoo Cat#: 146280

Name: Allysine

CAS#: 6665-12-9

Chemical Formula: C6H11NO3

Exact Mass: 145.0739

Molecular Weight: 145.16

Elemental Analysis: C, 49.65; H, 7.64; N, 9.65; O, 33.07

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
Allysine;
IUPAC/Chemical Name
(S)-2-amino-6-oxohexanoic acid
InChi Key
GFXYTQPNNXGICT-YFKPBYRVSA-N
InChi Code
1S/C6H11NO3/c7-5(6(9)10)3-1-2-4-8/h4-5H,1-3,7H2,(H,9,10)/t5-/m0/s1
SMILES Code
N[C@@H](CCCC=O)C(O)=O
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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 145.16 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: Ma H, Esfahani SA, Krishna S, Ataeinia B, Zhou IY, Rotile NJ, Weigand- Whittier J, Boice AT, Liss AS, Tanabe KK, Caravan P. Allysine-Targeted Molecular MRI Enables Early Prediction of Chemotherapy Response in Pancreatic Cancer. Cancer Res. 2024 Aug 1;84(15):2549-2560. doi: 10.1158/0008-5472.CAN-23-3548. PMID: 38759082; PMCID: PMC11293968. 2: Zhuang Y, Yin T, Li J, Zang Y, Li X. An Allysine-Conjugatable Probe for Fluorogenically Imaging Fibrosis. Anal Chem. 2024 Jun 4;96(22):9034-9042. doi: 10.1021/acs.analchem.4c00404. Epub 2024 May 21. PMID: 38773734. 3: Ozsvar J, Tarakanova A, Wang R, Buehler MJ, Weiss AS. Allysine modifications perturb tropoelastin structure and mobility on a local and global scale. Matrix Biol Plus. 2019 Mar 12;2:100002. doi: 10.1016/j.mbplus.2019.03.001. PMID: 33543005; PMCID: PMC7852328. 4: Luna C, Arjona A, Dueñas C, Estevez M. Allysine and α-Aminoadipic Acid as Markers of the Glyco-Oxidative Damage to Human Serum Albumin under Pathological Glucose Concentrations. Antioxidants (Basel). 2021 Mar 17;10(3):474. doi: 10.3390/antiox10030474. PMID: 33802856; PMCID: PMC8002732. 5: Emenike B, Shahin S, Raj M. Bioinspired Synthesis of Allysine for Late-Stage Functionalization of Peptides. Angew Chem Int Ed Engl. 2024 May 27;63(22):e202403215. doi: 10.1002/anie.202403215. Epub 2024 Mar 26. PMID: 38529755; PMCID: PMC11254099. 6: Luna C, Estévez M. Formation of allysine in β-lactoglobulin and myofibrillar proteins by glyoxal and methylglyoxal: Impact on water-holding capacity and in vitro digestibility. Food Chem. 2019 Jan 15;271:87-93. doi: 10.1016/j.foodchem.2018.07.167. Epub 2018 Jul 25. PMID: 30236745. 7: Shuvaev S, Knipe RS, Drummond M, Rotile NJ, Ay I, Weigand-Whittier JP, Ma H, Zhou IY, Roberts JD Jr, Black K, Hariri LP, Ning Y, Caravan P. Optimization of an Allysine-Targeted PET Probe for Quantifying Fibrogenesis in a Mouse Model of Pulmonary Fibrosis. Mol Imaging Biol. 2023 Oct;25(5):944-953. doi: 10.1007/s11307-023-01845-2. Epub 2023 Aug 23. PMID: 37610609. 8: Wahsner J, Désogère P, Abston E, Graham-O'Regan KA, Wang J, Rotile NJ, Schirmer MD, Santos Ferreira DD, Sui J, Fuchs BC, Lanuti M, Caravan P. 68Ga-NODAGA-Indole: An Allysine-Reactive Positron Emission Tomography Probe for Molecular Imaging of Pulmonary Fibrogenesis. J Am Chem Soc. 2019 Apr 10;141(14):5593-5596. doi: 10.1021/jacs.8b12342. Epub 2019 Mar 27. PMID: 30908032; PMCID: PMC6494104. 9: Ahmed F, Kleffmann T, Husain M. Acetylation, Methylation and Allysine Modification Profile of Viral and Host Proteins during Influenza A Virus Infection. Viruses. 2021 Jul 20;13(7):1415. doi: 10.3390/v13071415. PMID: 34372620; PMCID: PMC8310381. 10: Wang ZA, Zeng Y, Kurra Y, Wang X, Tharp JM, Vatansever EC, Hsu WW, Dai S, Fang X, Liu WR. A Genetically Encoded Allysine for the Synthesis of Proteins with Site-Specific Lysine Dimethylation. Angew Chem Int Ed Engl. 2017 Jan 2;56(1):212-216. doi: 10.1002/anie.201609452. Epub 2016 Dec 2. PMID: 27910233; PMCID: PMC5206893. 11: Chen YC, Waghorn PA, Rosales IA, Arora G, Erstad DJ, Rotile NJ, Jones CM, Ferreira DS, Wei L, Martinez RVP, Schlerman FJ, Wellen J, Fuchs BC, Colvin RB, Ay I, Caravan P. Molecular MR Imaging of Renal Fibrogenesis in Mice. J Am Soc Nephrol. 2023 Jul 1;34(7):1159-1165. doi: 10.1681/ASN.0000000000000148. Epub 2023 Apr 24. PMID: 37094382; PMCID: PMC10356170. 12: Waghorn PA, Oliveira BL, Jones CM, Tager AM, Caravan P. High sensitivity HPLC method for determination of the allysine concentration in tissue by use of a naphthol derivative. J Chromatogr B Analyt Technol Biomed Life Sci. 2017 Oct 1;1064:7-13. doi: 10.1016/j.jchromb.2017.08.032. Epub 2017 Aug 26. PMID: 28886479; PMCID: PMC5662445. 13: Dölz R, Heidemann E. Reactivity of the allysine aldehyde group. Connect Tissue Res. 1989;18(4):255-68. doi: 10.3109/03008208909019075. PMID: 2743767. 14: Umeda H, Kawamorita K, Suyama K. High-performance liquid chromatographic quantification of allysine as bis-p-cresol derivative in elastin. Amino Acids. 2001;20(2):187-99. doi: 10.1007/s007260170059. PMID: 11332453. 15: Guo M, Liu D, Jiang Y, Chen W, Zhao L, Bao D, Li Y, Distler JHW, Zhu H. Serum metabolomic profiling reveals potential biomarkers in systemic sclerosis. Metabolism. 2023 Jul;144:155587. doi: 10.1016/j.metabol.2023.155587. Epub 2023 May 6. PMID: 37156409. 16: Ma H, Zhou IY, Chen YI, Rotile NJ, Ay I, Akam EA, Wang H, Knipe RS, Hariri LP, Zhang C, Drummond M, Pantazopoulos P, Moon BF, Boice AT, Zygmont SE, Weigand-Whittier J, Sojoodi M, Gonzalez-Villalobos RA, Hansen MK, Tanabe KK, Caravan P. Tailored Chemical Reactivity Probes for Systemic Imaging of Aldehydes in Fibroproliferative Diseases. J Am Chem Soc. 2023 Sep 27;145(38):20825-20836. doi: 10.1021/jacs.3c04964. Epub 2023 Aug 17. PMID: 37589185; PMCID: PMC11022681. 17: Yan J, Wu J, Xu M, Wang M, Guo W. Disrupted de novo pyrimidine biosynthesis impairs adult hippocampal neurogenesis and cognition in pyridoxine-dependent epilepsy. Sci Adv. 2024 Apr 5;10(14):eadl2764. doi: 10.1126/sciadv.adl2764. Epub 2024 Apr 5. PMID: 38579001; PMCID: PMC10997211. 18: Oitate M, Hirota T, Murai T, Miura S, Ikeda T. Covalent binding of rofecoxib, but not other cyclooxygenase-2 inhibitors, to allysine aldehyde in elastin of human aorta. Drug Metab Dispos. 2007 Oct;35(10):1846-52. doi: 10.1124/dmd.107.016121. Epub 2007 Jul 9. PMID: 17620346. 19: Hanson RL, Howell JM, LaPorte TL, Donovan MJ, Cazzulino DL, Zannella V V, Montana MA, Nanduri VB, Schwarz SR, Eiring RF, Durand SC, Wasylyk JM, Parker WL, Liu MS, Okuniewicz FJ, Chen B, Harris JC, Natalie KJ, Ramig K, Swaminathan S, Rosso VW, Pack SK, Lotz BT, Bernot PJ, Rusowicz A, Lust DA, Tse KS, Venit JJ, Szarka LJ, Patel RN. Synthesis of allysine ethylene acetal using phenylalanine dehydrogenase from Thermoactinomyces intermedius. Enzyme Microb Technol. 2000 Mar 1;26(5-6):348-358. doi: 10.1016/s0141-0229(99)00175-1. PMID: 10713207. 20: Bouchereau J, Schiff M. Inherited Disorders of Lysine Metabolism: A Review. J Nutr. 2020 Oct 1;150(Suppl 1):2556S-2560S. doi: 10.1093/jn/nxaa112. PMID: 33000154.