14108-60-2

Basic information

• Product Name: H-DL-2-NAL-OH
• Synonyms: 3-(2-NAPHTHYL)-DL-ALANINE;2-AMINO-3-NAPHTHALEN-2-YL-PROPIONIC ACID;H-DL-NAL(2)-OH;H-DL-ALA(2-NAPH)-OH;H-DL-ALA(2-NAPHTHYL)-OH;H-DL-2-NAL-OH;DL-3-(2-NAPHTHYL)ALANINE;2-amino-3-naphthalen-2-ylpropanoic acid
• CAS NO: 14108-60-2
• Molecular Formula: C₁₃H₁₃NO₂
• Molecular Weight: 215.25
• Product Categories: Peptide;I - Z;Modified Amino Acids;Amino Acids
• Mol File: 14108-60-2.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 412.3 °C at 760 mmHg
• Flash Point: 203.2 °C
• Appearance: Off-white/Powder
• Density: 1.254
• Vapor Pressure: 1.54E-07mmHg at 25°C
• Refractive Index: 1.66
• Storage Temp.: 2-8°C
• Solubility: Aqueous Base (Slightly)
• PKA: 2.21±0.30(Predicted)
• CAS DataBase Reference: H-DL-2-NAL-OH(CAS DataBase Reference)
• NIST Chemistry Reference: H-DL-2-NAL-OH(14108-60-2)
• EPA Substance Registry System: H-DL-2-NAL-OH(14108-60-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 14108-60-2(Hazardous Substances Data)

Usage

Description

H-DL-2-NAL-OH, also known as Hydroxy-DL-Norsalsolinol, is a white powder chemical compound that serves as a precursor in the synthesis of ergoline alkaloids. It is derived from the Claviceps species, which are fungi that produce ergot alkaloids. H-DL-2-NAL-OH is known for its ability to induce the formation of ergoline alkaloids in submerged cultures of Claviceps species, making it a valuable component in the pharmaceutical industry.

Uses

Used in Pharmaceutical Industry:
H-DL-2-NAL-OH is used as a precursor for the synthesis of ergoline alkaloids for various pharmaceutical applications. The expression is: H-DL-2-NAL-OH is used as a precursor for [synthesis of ergoline alkaloids] for [inducing the formation of ergoline alkaloids in submerged cultures of Claviceps species].
Used in Research and Development:
H-DL-2-NAL-OH is also used in research and development for studying the biosynthesis of ergoline alkaloids and their potential applications in medicine. The expression is: H-DL-2-NAL-OH is used as a research compound for [studying the biosynthesis of ergoline alkaloids and their potential applications] for [enhancing the understanding of ergoline alkaloid production and their therapeutic uses].

InChI:InChI=1/C13H13NO2/c14-12(13(15)16)8-9-5-6-10-3-1-2-4-11(10)7-9/h1-7,12H,8,14H2,(H,15,16)

Upstream product

• 37439-99-9 (S)-N-acetyl-3-(2-naphthyl)alanine 
• 56-40-6 glycine 
• 939-26-4 2-bromomethylnaphthyl bromide 
• 109063-69-6 (S)-methyl 2-amino-3-(naphthalen-2-yl)propanoate 
• 14108-60-2 2-amino-3-(2-naphthyl)propanoic acid 
• 136015-50-4 2-Acetylamino-2-naphthalen-2-ylmethyl-malonic acid monoethyl ester 
• 139040-38-3 1,1,1-Trichloro-3-naphthalen-2-yl-propan-2-one 
• 139040-43-0 (R)-1,1,1-Trichloro-3-naphthalen-2-yl-propan-2-ol 
• 37447-33-9 acetylamino-[2]naphthylmethyl-malonic acid diethyl ester 
• 172214-89-0 2-Acetylamino-3-naphthalen-2-yl-propionic acid ethyl ester 
• 603944-76-9 (±)-ethyl 2-amino-3-(naphthalen-2-yl)propanoate 
• 37439-99-9 (RS)-N-acetyl-2-naphthylalanine 
• 111726-64-8 3-(naphthalene-2-yl)-2-oxopropanoic acid 
• 49711-14-0 (E)-3-(naphthalen-2-yl)acrylic acid 

Downstream Products

• 63024-26-0 methyl (S)-2-amino-3-(naphthalen-2-yl)propanoate hydrochloride 
• 56583-58-5 N-tert-butoxycarbonyl-3-(2-naphthyl)-L-alanine 
• 65365-16-4 L-N-benzyloxycarbonyl-3-(2-naphthyl)alanine 
• 6960-34-5 L-3-(2-naphthyl)alanine 
• 111726-64-8 3-(naphthalene-2-yl)-2-oxopropanoic acid 
• 894407-00-2 (3S,4S)-3-[(tert-butyl)dimethylsiloxy]-5-(2-naphthyl)-4-[N-(2-nitrobenzenesulfonyl)amino]pent-1-ene 
• 894407-04-6 (5S,6S)-1-[4-(tert-butoxycarbonylamino)butyl]-5,6-dihydro-5-diphenylphosphoryloxy-6-[(2-naphthyl)methyl]pyridin-2-one 
• 894407-01-3 (3S,4S)-4-{N-[4-(tert-butoxycarbonylamino)butyl]-N-(2-nitrobenzenesulfonyl)}amino-3-[(tert-butyl)dimethylsiloxy]-5-(2-naphthyl)pent-1-ene 
• 176896-73-4 methyl (S)-2-[(tert-butoxycarbonyl)amino]-3-(naphthalen-2-yl)propanoate 

Relevant articles and documents

Drug Design Inspired by Nature: Crystallographic Detection of an Auto-Tailored Protease Inhibitor Template

De novo drug discovery is still a challenge in the search for potent and selective modulators of therapeutically relevant target proteins. Here, we disclose the unexpected discovery of a peptidic ligand 1 by X-ray crystallography, which was auto-tailored by the therapeutic target MMP-13 through partial self-degradation and subsequent structure-based optimization to a highly potent and selective β-sheet peptidomimetic inhibitor derived from the endogenous tissue inhibitors of metalloproteinases (TIMPs). The incorporation of non-proteinogenic amino acids in combination with a cyclization strategy proved to be key for the de novo design of TIMP peptidomimetics. The optimized cyclic peptide 4 (ZHAWOC7726) is membrane permeable with an IC50 of 21 nm for MMP-13 and an attractive selectivity profile with respect to a polypharmacology approach including the anticancer targets MMP-2 (IC50: 170 nm) and MMP-9 (IC50: 140 nm).

Asymmetric Transamination of α-Keto Acids Catalyzed by Chiral Pyridoxamines

A new type of novel chiral pyridoxamines 3a-g containing a side chain has been developed. The pyridoxamines displayed catalytic activity and promising enantioselectivity in biomimetic asymmetric transamination of α-keto acids, to give various α-amino acids in 47-90% yields with up to 87% ee's under very mild conditions. An interesting effect of the side chain on enantioselectivity was observed in the reaction.

Convenient method for reduction of C-N double bonds in oximes, imines, and hydrazones using sodium Borohydride-Raney ni system

(Chemical Equation Presented) A practical method has been developed for reduction of C-N double bond in oximes, imines, and hydrazones with sodium borohydride catalyzed by Raney Ni. The reactions were carried out in basic aqueous solution, and the desired products were obtained in moderate yields after a simple procedure. This method can be applied to synthesize simpler aliphatic or aromatic amines and its analogs. Copyright Taylor & Francis Group, LLC.