88930-14-7

Basic information

• Product Name: H-D-Me-Val-OH
• Synonyms: N-Methyl-D-valine;D-N-Me-val / N-Me-D-val
• CAS NO: 88930-14-7
• Molecular Formula: C₆H₁₃NO₂
• Molecular Weight: 131.17
• Mol File: 88930-14-7.mol

Chemical Properties

• Boiling Point: 206.9 °C at 760 mmHg
• Flash Point: 78.9 °C
• Appearance: /
• Density: 0.995
• Vapor Pressure: 0.0935mmHg at 25°C
• Refractive Index: 1.442
• PKA: 2.38±0.13(Predicted)
• CAS DataBase Reference: H-D-Me-Val-OH(CAS DataBase Reference)
• NIST Chemistry Reference: H-D-Me-Val-OH(88930-14-7)
• EPA Substance Registry System: H-D-Me-Val-OH(88930-14-7)

Safety Data

• Hazardous Substances Data: 88930-14-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
H-D-Me-Val-OH is used as a key component in the synthesis of pharmaceuticals for its antimicrobial, antifungal, and antitumor properties. Its unique structure allows it to be incorporated into the development of new drugs and therapeutic agents that target a variety of diseases and conditions.
Used in Bioactive Compounds Synthesis:
H-D-Me-Val-OH is used as a building block in the synthesis of bioactive compounds due to its biological activities. Its presence in naturally occurring peptides and antibiotics highlights its potential in creating new molecules with therapeutic benefits.
Used in Drug Development:
H-D-Me-Val-OH is used as a valuable molecule in drug development for its demonstrated biological activities. Researchers leverage its unique properties to create innovative treatments and therapies that address unmet medical needs.
Used in Medicinal Chemistry:
H-D-Me-Val-OH is used as a crucial element in medicinal chemistry for its potential to contribute to the discovery and design of new drugs. Its optical isomerism and non-proteinogenic nature offer a distinct advantage in the exploration of novel chemical spaces and therapeutic targets.

InChI:InChI=1/C6H13NO2/c1-4(2)5(7-3)6(8)9/h4-5,7H,1-3H3,(H,8,9)/t5-/m1/s1

Upstream product

• 1494680-68-0 ohmyungsamycin A 

Downstream Products

• 812788-74-2 (3R,6S)-3,6-diisopropyl-4-methyl-2,5-morpholinedione 
• 56346-69-1 N-methyl-N-chloroacetyl-DL-valine 
• 859800-36-5 N-methyl-N-DL-phenylacetyl-valine 
• 92619-25-5 N-Me-Cbz-valine 
• 408507-19-7 3-(N-methylamino)-4-methyl-2-pentanone 
• 42417-65-2 Z-MeVal-OH 
• 53978-73-7 Z-D-MeVal 
• 899900-52-8 (R)-2-(N,N-dimethylamino)-3-methylbutanoic acid 
• 847927-42-8 L-DLA-N-Me-D-Val 
• 194736-84-0 FDAA-D-NMe-Val 
• 39554-30-8 NZ-D-Val(Me)-HyiV-OtBu 
• 19892-98-9 O-<(4-Nitro-benzyloxycarbonyl)-N-methyl-D-valin>-D-2-hydroxy-isovaleriansaeure-tert.-butylester 
• 39554-32-0 NZ-D-Val(Me)-HyiV 
• 39606-21-8 NZ-D-Val(Me)-D-HyiV 

Relevant articles and documents

Isolation and Total Synthesis of Mabuniamide, a Lipopeptide from an Okeania sp. Marine Cyanobacterium

The bioassay-guided fractionation of an Okeania sp. marine cyanobacterium collected in Okinawa led to the isolation of the lipopeptide mabuniamide (1). The gross structure of 1 was determined by spectroscopic analyses, and its absolute configuration was determined using Marfey's analysis of the acid hydrolysate of 1. The absolute configuration of 1 was confirmed by total synthesis. Mabuniamide (1) stimulated glucose uptake in cultured rat L6 myotubes. In addition, mabuniamide (1) and its stereoisomer (2) exhibited moderate antimalarial activity.

Discovery of Amantamide, a Selective CXCR7 Agonist from Marine Cyanobacteria

CXCR7 plays an emerging role in several physiological processes. A linear peptide, amantamide (1), was isolated from marine cyanobacteria, and the structure was determined by NMR and mass spectrometry. The total synthesis was achieved by solid-phase method. After screening two biological target libraries, 1 was identified as a selective CXCR7 agonist. The selective activation of CXCR7 by 1 could provide the basis for developing CXCR7-targeted therapeutics and deciphering the role of CXCR7 in different diseases.

Dudawalamides A-D, Antiparasitic Cyclic Depsipeptides from the Marine Cyanobacterium Moorea producens

A family of 2,2-dimethyl-3-hydroxy-7-octynoic acid (Dhoya)-containing cyclic depsipeptides, named dudawalamides A-D (1-4), was isolated from a Papua New Guinean field collection of the cyanobacterium Moorea producens using bioassay-guided and spectroscopic approaches. The planar structures of dudawalamides A-D were determined by a combination of 1D and 2D NMR experiments and MS analysis, whereas the absolute configurations were determined by X-ray crystallography, modified Marfey's analysis, chiral-phase GCMS, and chiral-phase HPLC. Dudawalamides A-D possess a broad spectrum of antiparasitic activity with minimal mammalian cell cytotoxicity. Comparative analysis of the Dhoya-containing class of lipopeptides reveals intriguing structure-activity relationship features of these NRPS-PKS-derived metabolites and their derivatives.

Ohmyungsamycins A and B: Cytotoxic and antimicrobial cyclic peptides produced by Streptomyces sp. from a volcanic island

Ohmyungsamycins A and B (1 and 2), which are new cyclic peptides, were isolated from a marine bacterial strain belonging to the Streptomyces genus collected from a sand beach on Jeju, a volcanic island in the Republic of Korea. Based on the interpretation of the NMR, UV, and IR spectroscopic and MS data, the planar structures of 1 and 2 were elucidated as cyclic depsipeptides bearing unusual amino acid units, including N-methyl-4-methoxytrytophan, β-hydroxyphenylalanine, and N,N-dimethylvaline. The absolute configurations of the α-carbons of the amino acid residues were determined using the advanced Marfey's method. The configurations of the additional stereogenic centers at the β-carbons of the threonine, N-methylthreonine, and β-hydroxyphenylalanine units were assigned by GITC (2,3,4,6-tetra-O-acetyl- β-d-glucopyranosyl isothiocyanate) derivatization and the modified Mosher's method. We have developed a new method utilizing PGME (phenylglycine methyl ester) derivatization coupled with chromatographic analysis to determine the absolute configuration of N,N-dimethylvaline. Our first successful establishment of the absolute configuration of N,N-dimethylvaline using PGME will provide a general and convenient analytical method for determining the absolute configurations of amino acids with fully substituted amine groups. Ohmyungsamycins A and B showed significant inhibitory activities against diverse cancer cells as well as antibacterial effects.

Two new 14-membered cyclopeptide alkaloids from Zizyphus xylopyra

The phytochemical investigation of the bark of Zizyphus xylopyra resulted in the isolation of two new 14-membered ring cyclopeptide alkaloids, xylopyrine-G and xylopyrine H. Their structures have been established by chemical and spectral evidences.