19764-31-9

Basic information

• Product Name: 2-acetamido-3-methyl-pentanoic acid
• Synonyms: Isoleucine, N-acetyl-, D-;Nsc203806;(2R,3R)-2-acetamido-3-methylpentanoic acid
• CAS NO: 19764-31-9
• Molecular Formula: C₈H₁₅NO₃
• Molecular Weight: 173.2096
• Mol File: 19764-31-9.mol

Chemical Properties

• Boiling Point: 369.7°Cat760mmHg
• Flash Point: 177.4°C
• Appearance: /
• Density: 1.069g/cm³
• Vapor Pressure: 1.77E-06mmHg at 25°C
• Refractive Index: 1.458
• CAS DataBase Reference: 2-acetamido-3-methyl-pentanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-acetamido-3-methyl-pentanoic acid(19764-31-9)
• EPA Substance Registry System: 2-acetamido-3-methyl-pentanoic acid(19764-31-9)

Safety Data

• Hazardous Substances Data: 19764-31-9(Hazardous Substances Data)

Usage

General Description

The chemical compound "2-acetamido-3-methyl-pentanoic acid" is a derivative of pentanoic acid, with an additional acetamido and methyl group attached to the third carbon atom. It is a white crystalline solid with a molecular formula of C8H15NO3 and a molar mass of 173.21 g/mol. 2-acetamido-3-methyl-pentanoic acid is commonly used in organic synthesis and pharmaceutical research, particularly in the development of new medications. It may also have applications in the field of biochemistry and biotechnology, as it can potentially be used as a building block for more complex molecules with specific biological activities. Additionally, it is important to handle this chemical compound with care, as it may pose various health and safety risks if mishandled.

InChI:InChI=1/C8H15NO3/c1-4-5(2)7(8(11)12)9-6(3)10/h5,7H,4H2,1-3H3,(H,9,10)(H,11,12)

Upstream product

• 73-32-5 L-isoleucine 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 1509-35-9 D-alloisoleucine 
• 959215-79-3 (2RS,3S)-2-amino-3-methylpentanoic acid 
• 1565-80-6 (2S)-2-methyl-1-butanol 
• 319-78-8 D-Isoleucine 
• 3107-04-8 DL-alloisoleucine 
• 73-32-5 DL-isoleucine 
• 60-35-5 acetamide 
• 624-64-6 trans-2-Butene 
• 201230-82-2 carbon monoxide 
• 2516-33-8 Cyclopropylmethanol 
• 2256-90-8 ethyl N-acetyl-isoleucinate 

Downstream Products

• 4819-22-1 N-Acetyl-DL-isoleucin-ethylester 
• 312746-55-7 Ac-ISVU(Ph)RSTS 
• 488-15-3 (2S,3S)-2-Hydroxy-3-methylpentanoic acid 
• 1233083-92-5 2-acetylamino-3-methylpentanoic acid (5-benzyl-14,17-di-sec-butyl-4,7,13,16,19-pentaoxo-eicosahydro-3a,6,12,15,18-pentaaza-cyclopentacyclooctadecen-8-yl)amide 
• 1233083-94-7 pseudacyclin B 
• 319-78-8 D-Isoleucine 
• 488-15-3 (2R,3R)-2-hydroxy-3-methylpentanoic acid 
• 73-32-5 L-isoleucine 
• 857027-07-7 imidazolide 
• 1509-34-8 D-allo-isoleucine 
• 54831-20-8 (2R,3S)-2-acetamido-3-methylpentanoic acid 
• 205807-93-8 N-acetyl-L-isoleucyl-L-phenylalanine methyl ester 

Relevant articles and documents

Structures and properties of a diastereoisomeric molecular compound of (2S,3S)- and (2R,3S)-N-acetyl-2-amino-3-methylpentanoic acids

An X-ray crystal structural analysis revealed that (2S,3S)-N-acetyl-2- amino-3-methylpentanoic acid (N- acetyl-l-isoleucine; Ac-l-I1e) and (2R,3S)-N-acetyl-2- amino-3-methylpentanoic acid (N-acetyl-d-alloisoleucine; Ac-d-aIle) formed a molecular compound containing one Ac-l-Ile molecule and one Ac-d-aIle molecule as an unsymmetrical unit. This molecular compound is packed with strong hydrogen bonds forming homogeneous chains consisting of Ac-l-Ile molecules or Ac-d- aIle molecules and weak hydrogen bonds connecting these homogeneous chains in a fashion similar to that observed for Ac-l-Ile and Ac-d-aIle. Recrystallization of an approximately 1:1 mixture of Ac-l-Ile and Ac-d-aIle from water gave an equimolar molecular compound due to its lower solubility than that of Ac-d-aIle or especially Ac-l-Ile. The results suggest that the equimolar mixture of Ac-l-Ile and Ac-d-aIle could be obtained from an Ac-l-Ile-excess mixture by recystallization from water.

Structure-activity relationship studies of dipeptide-based hepsin inhibitors with Arg bioisosteres

Hepsin is a type II transmembrane serine protease (TTSP) associated with cell proliferation and overexpressed in several types of cancer including prostate cancer (PCa). Because of its significant role in cancer progression and metastasis, hepsin is an attractive protein as a potential therapeutic and diagnostic biomarker for PCa. Based on the reported Leu-Arg dipeptide-based hepsin inhibitors, we performed structural modification and determined in vitro hepsin- and matriptase-inhibitory activities. Comprehensive structure-activity relationship studies identified that the p-guanidinophenylalanine-based dipeptide analog 22a exhibited a strong hepsin-inhibitory activity (Ki = 50.5 nM) and 22-fold hepsin selectivity over matriptase. Compound 22a could be a prototype molecule for structural optimization of dipeptide-based hepsin inhibitors.

Bio- And Medicinally Compatible α-Amino-Acid Modification via Merging Photoredox and N-Heterocyclic Carbene Catalysis

An N-heterocyclic carbene and photoredox cocatalyzed α-amino-acid decarboxylative carbonylation reaction is presented. This method displays good scope generality, providing a direct pathway to access various downstream α-amino ketones under bio- and medicinally compatible conditions. Moreover, this strategy is appealing to chemical biology because it has great potential for the chemical modification of peptides or the late-stage synthesis of keto-peptides.

Oxidative Damage in Aliphatic Amino Acids and Di- and Tripeptides by the Environmental Free Radical Oxidant NO3?: the Role of the Amide Bond Revealed by Kinetic and Computational Studies

Kinetic and computational data reveal a complex behavior of the important environmental free radical oxidant NO3? in its reactions with aliphatic amino acids and di- and tripeptides, suggesting that attack at the amide N-H bond in the peptide backbone is a highly viable pathway, which proceeds through a proton-coupled electron transfer (PCET) mechanism with a rate coefficient of about 1 × 106 M-1 s-1 in acetonitrile. Similar rate coefficients were determined for hydrogen abstraction from the α-carbon and from tertiary C-H bonds in the side chain. The obtained rate coefficients for the reaction of NO3? with aliphatic di- and tripeptides suggest that attack occurs at all of these sites in each individual amino acid residue, which makes aliphatic peptide sequences highly vulnerable to NO3?-induced oxidative damage. No evidence for amide neighboring group effects, which have previously been found to facilitate radical-induced side-chain damage in phenylalanine, was found for the reaction of NO3? with side chains in aliphatic peptides.

GRANZYME B DIRECTED IMAGING AND THERAPY

Provided herein are heterocyclic compounds useful for imaging Granzyme B. Methods of imaging Granzyme B, combination therapies, and kits comprising the Granzyme B imaging agents are also provided.

Rapid Room-Temperature Gelation of Crude Oils by a Wetted Powder Gelator

Phase-selective organogelators (PSOGs) not only exhibit ability to phase-selectively congeal oil from oily water but also allow easy separation of gelled oil from the body of water. However, all hitherto reported PSOGs either necessitate carrier solvents for their dissolution or suffer from an extremely slow action in gelling oil in the powder form. A previously unexplored generally applicable wetting strategy is now described to dramatically enhance, by up to two orders of magnitude, gelling speed of the resultant wet but non-sticky gelator in the powder form in crude oils of widely ranging viscosities. Such unprecedented rapid gelling speeds enable rapid gelation of six types of (un)weathered crude oils within minutes at room temperature, making PSOGs one step closer to their eventual practical uses as one of important oil spill control technologies.

AN ORGANOGELATOR COMPOUND

An organogelator compound is provided. The organogelator compound has Formula (I): wherein R1, R2, and R3 are independently selected from the group consisting of H, halogen, a substituted or unsubstituted C1-C20 alkyl, a substituted or unsubstituted C1-C20 alkoxy, a substituted or unsubstituted C2-C20 alkenyl, a substituted or unsubstituted C2-C20 alkynyl, a substituted or unsubstituted C3-C20 alicyclic group, a substituted or unsubstituted C5-C15 aryl, a substituted or unsubstituted C6-C30 alkyl-aryl, a substituted or unsubstituted C3-C20 heterocycle, a substituted or unsubstituted C4-C30 alkyl-heterocycle, a substituted or unsubstituted C5-C15 heteroaryl, -NRR', -NR, -OR, -SR, -CN, -NO2, -C(O)-R, -COOR, -NR'- C(O)-R, -C(O)-NRR', -C(NR)-R', -SO2-R, -(SO2)-OR, -C(S)-R, and -C(S)-NRR'; and R and R' are independently selected from the group consisting of H, halogen, a substituted or unsubstituted C1-C20 alkyl, a substituted or unsubstituted C1-C20 alkoxy, a substituted or unsubstituted C2-C20 alkenyl, a substituted or unsubstituted C2-C20 alkynyl, and a substituted or unsubstituted C5-C15 aryl. A method of gelating an oil and an organic solvent having a Polarity Index of less than 3 is also provided.

Jamaicensamide A, a Peptide Containing β-Amino-α-keto and Thiazole-Homologated η-Amino Acid Residues from the Sponge Plakina jamaicensis

A new cyclic peptide, jamaicensamide A, composed of six amino acids, including a thiazole-homologated amino acid, was isolated from the Bahamian sponge Plakina jamaicensis, along with known compounds bitungolide A and franklinolide A. The structure of the title peptide was solved by integrated analysis of MS, 1D and 2D NMR data, oxidation-hydrolyses to α-amino acids, and their stereodetermination by Marfey's method. The close structural resemblance of Western Atlantic-derived jamaicensamide A to known Western Pacific-derived peptides of lithistid sponges in the genus Theonella and Discodermia suggests a common origin: the symbiotic bacterium Entotheonella sp., a so-called "talented producer" responsible for biosynthesis of most Theonella-associated peptides. Similar natural products from sponges of disparate genera evince the likelihood that these invertebrates harbor the same or a very similar symbiont.

Peptide Tyrosinase Activators

Peptides that increase melanin synthesis are provided. These peptides include pentapeptides YSSWY, YRSRK, and their variants. The peptides may activate the enzymatic activity of tyrosinase to increase melanin synthesis. The pharmaceutical, cosmetic, and other compositions including the peptides are also provided. The methods of increasing melanin production in epidermis of a subject are provided where the methods include administering compositions comprising an amount of one or more peptides effective to increase the melanin production. The methods also include treating vitiligo or other hypopigmentation disorders with compositions including one or more peptides.

Aqueous MW eco-friendly protocol for amino group protection

In this paper a new catalyst-free and on-water method for protection of amines and amino acids with di-tert-butyl dicarbonate, 9-fluorenylmethoxycarbonyl chloride, acetyl chloride and tosyl chloride is presented. The protection can be realized in a few minutes under microwave-assistance. The reaction proved to be chemoselective in presence of ambident nucleophiles and water solution of di-tert-butyl carboxylic acid or chloride acid are the only wastes produced.