56-88-2

Basic information

• Product Name: L-CYSTATHIONINE
• Synonyms: L-CYSTATHIONINE, >= 98% (TLC);CYSTATHIONINE, L-;L(+)CYSTATHIONINE;L-CYSTATHIONINE;[R]-S-[2-AMINO-2-CARBOXYETHYL]-L-HOMOCYSTEINE;(2S)-2-amino-4-[(2R)-2-amino-3-hydroxy-3-oxopropyl]sulfanylbutanoic acid;(2R,7S)-2,7-Diamino-4-thiaoctanedioic acid;S-[(R)-2-Amino-2-carboxyethyl]-L-homocysteine
• CAS NO: 56-88-2
• Molecular Formula: C₇H₁₄N₂O₄S
• Molecular Weight: 222.26
• EINECS: 200-295-8
• Product Categories: Amino Acids 13C, 2H, 15N;Amino Acids & Derivatives;Intermediates;Sulfur & Selenium Compounds
• Mol File: 56-88-2.mol
• Article Data: 9

Chemical Properties

• Melting Point: 312
• Boiling Point: 481 °C at 760 mmHg
• Flash Point: 244.7 °C
• Appearance: White Crystalline Solid
• Density: 1.430±0.06 g/cm3 (20 ºC 760 Torr)
• Refractive Index: 1.592
• Storage Temp.: −20°C
• Solubility: Aqueous Acid (Slightly)
• PKA: 2.08±0.10(Predicted)
• Merck: 13,2807
• BRN: 2505200
• CAS DataBase Reference: L-CYSTATHIONINE(CAS DataBase Reference)
• NIST Chemistry Reference: L-CYSTATHIONINE(56-88-2)
• EPA Substance Registry System: L-CYSTATHIONINE(56-88-2)

Safety Data

• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 56-88-2(Hazardous Substances Data)

Usage

Chemical Description

L-cystathionine and L-allocystathionine are amino acids that are synthesized in the experiment.

Description

L-(+)-Cystathionine is a dipeptide formed by serine and homocysteine. Transsulfuration of methionine yields homocysteine, which combines with serine to form this precursor of cysteine. L-(+)-Cystathionine is largely expressed in the mammalian brain and deficiency can indicate the presence of metabolic disorders such as cystathioninuria.

Chemical Properties

White Crystalline Solid

Uses

Different sources of media describe the Uses of 56-88-2 differently. You can refer to the following data:
1. Intermediate in transsulfuration whereby the mammal transfers the sulfur of methionine via homocysteine to cysteine
2. L-Cystathionine has been used in ultra-performance liquid chromatography for the validation of cystathionine and the correlation of its abundance with vertebrate metamorphosis. It has also been used as an inhibitor of sinusoidal GSH (glutathione) carrier to signify that thiol redox state imbalance is associated with the modulation of autophagy in carcinoma cells.

Biochem/physiol Actions

L-Cystathionine is an intermediate in the biosynthesis of L-cysteine and methionine. It is used as a substrate to differentiate and analyze cystathionine γ-lyase(s). L-Cystathionine is an important non-protein amino acid and is associated with metabolic disorders. In recent studies, L-cystathionine is believed to be the precursor of cyclic imino acid cyclothionine. Cystathioninuria is characterized with imino acid cyclothionine excretion in the urine.

Purification Methods

S,S-Cystathionine is purified by converting it to the HCl salt in 20% HCl and carefully basifying with aqueous NH3 until separation is complete. Filter it off and dry it in a vacuum. It forms prisms from H2O. The dibenzoyl derivative has m 229o (from EtOH). [IR: Greenstein & Winitz Chemistry of the Amino Acids (J Wiley) Vol 3 p2690 1961 and Tallan et al. J Biol Chem 230 707 1958, Synthesis: du Vigneaud et al. J Biol Chem 143 59 1942, Anslow et al. J Biol Chem 166 39 1946.] [Prepn: Weiss & Stekol J Am Chem Soc 73 2497 1951; see also du Vigneaud et al. J Biol Chem 143 60 1942, Biological synthesis: Greenberg Methods Enzymol 5 943 1962, Beilstein 4 IV 3197.]

InChI:InChI=1/C7H14N2O4S/c8-4(6(10)11)1-2-14-3-5(9)7(12)13/h4-5H,1-3,8-9H2,(H,10,11)(H,12,13)/t4-,5+/m1/s1

Upstream product

• 56-45-1 L-serin 
• 6027-13-0 L-homocysteine 
• 5429-56-1 N-Acetamidoacrylic acid 
• 56410-68-5 3-chloro-DL-alanine methyl ester 
• 454-29-5 2-amino-4-mercaptobutyric acid 
• 52-90-4 L-Cysteine 
• 407-41-0 L-phosphoserine 
• 2731-73-9 2-amino-3-chloropropanoic acid 
• 31828-68-9 L-homocysteine thiolactone hydrochloride 
• 51887-89-9 β-chloro-L-alanine hydrochloride 
• 672-15-1 L-homoserine 
• 56-89-3 L-cystine 
• 59-51-8 DL-methionine 
• 75189-61-6 N^α-tert-butyloxycarbonylcystathionine α'-methyl ester 

Downstream Products

• 94862-55-2 N,N'-dibenzoyl-L,L-cystathionine 
• 6027-13-0 L-homocysteine 
• 56-45-1 L-serin 
• 127-17-3 2-oxo-propionic acid 
• 1452573-76-0 4-[2-carboxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)-ethylsulfanyl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid 
• 85-87-0 pyridoxamine 
• 56-89-3 L-cystine 
• 52-90-4 L-Cysteine 
• 600-18-0 2-Oxobutyric acid 
• 7664-41-7 ammonia 
• 57-60-3 piruvate 
• 339-71-9 2-keto-butyrate 

Relevant articles and documents

Biogenesis of Hydrogen Sulfide and Thioethers by Cystathionine Beta-Synthase

Aims: The transsulfuration pathway enzymes cystathionine beta-synthase (CBS) and cystathionine gamma-lyase are thought to be the major source of hydrogen sulfide (H2S). In this study, we assessed the role of CBS in H2S biogenesis. Results: We show that despite discouraging enzyme kinetics of alternative H2S-producing reactions utilizing cysteine compared with the canonical condensation of serine and homocysteine, our simulations of substrate competitions at biologically relevant conditions suggest that cysteine is able to partially compete with serine on CBS, thus leading to generation of appreciable amounts of H2S. The leading H2S-producing reaction is condensation of cysteine with homocysteine, while cysteine desulfuration plays a dominant role when cysteine is more abundant than serine and homocysteine is limited. We found that the serine-to-cysteine ratio is the main determinant of CBS H2S productivity. Abundance of cysteine over serine, for example, in plasma, allowed for up to 43% of CBS activity being responsible for H2S production, while excess of serine typical for intracellular levels effectively limited such activity to less than 1.5%. CBS also produced lanthionine from serine and cysteine and a third of lanthionine coming from condensation of two cysteines contributed to the H2S pool. Innovation: Our study characterizes the H2S-producing potential of CBS under biologically relevant conditions and highlights the serine-to-cysteine ratio as the main determinant of H2S production by CBS in vivo. Conclusion: Our data clarify the function of CBS in H2S biogenesis and the role of thioethers as surrogate H2S markers.

Synthesis and evaluation of L-cystathionine as a standard for amino acid analysis

L-Cystathionine is a key nonprotein amino acid related to metabolic conditions. The quantitative determination of L-cystathionine in physiological fluids by amino acid analysis is important for clinical diagnosis; however, certified reference material for L-cystathionine with satisfactory purity, content, and quantity has been unavailable until recently. Consequently, a practical and simple method for the preparation of L-cystathionine was examined, which involves thioalkylation of N-tert-butoxycarbonyl-Lcysteine tert-butyl ester, derived from L-cystine, with (2S)-2-(tert-butoxycarbonyl)amino-4-iodobutanoic acid tert-butyl ester, derived from L-aspartic acid, to obtain L-cystathionine with protecting groups, followed by single-step deprotection under mild conditions. This method produces L-cystathionine in high purity (99.4%) and having sufficient percentage content according to amino acid analysis, which could be used as a standard for the amino acid analysis of physiological fluids.