L-Homocystine

한글명:L-Homocystine

카스 번호626-72-2

상품명:L-Homocystine

CBNumberCB5155903

분자식C8H16N2O4S2

포뮬러 무게268.35

MOL 파일626-72-2.mol

화학적 성질

녹는점	281-284 °C (dec.)(lit.)
알파	77 º (c=1% in 1N HCl)
끓는 점	507.6±50.0 °C(Predicted)
밀도	1.443±0.06 g/cm3(Predicted)
저장 조건	Keep in dark place,Inert atmosphere,Room temperature
용해도	H2O : 5 mg/mL (18.63 mM; ultrasonic and adjust pH to 3 with H2O)DMSO : 1 mg/mL (3.73 mM; ultrasonic and adjust pH to 5 with HCl)
물리적 상태	가루
산도 계수 (pKa)	1.90±0.10(Predicted)
BRN	1728583
InChIKey	ZTVZLYBCZNMWCF-WDSKDSINSA-N
CAS 데이터베이스	626-72-2(CAS DataBase Reference)
EPA	L-Homocystine (626-72-2)

위험 및 안전 성명

안전지침서	22-24/25
WGK 독일	3
HS 번호	29309090

L-Homocystine 화학적 특성, 용도, 생산

화학적 성질
L-homocysteine is an aliphatic amino acid with the molecular formula (C8H16N2O4S2). It is a white powder with an acidic taste and is easily soluble in water. It has limited solubility in ethanol. L-homocysteine has a sulfhydryl group on its side chain, which allows it to form disulfide bonds with other L-homocysteine residues in proteins. This feature contributes to the stable three-dimensional structure of proteins. As a result, L-homocysteine finds extensive applications in industries such as pharmaceuticals, food, feed, and cosmetics.
용도
Increased levels lead to hyperhomocysteinemia; a cardiovascular risk factor in prediction of coronary heart disease as well as being associated with congenital birth defects, pregnancy complications and cancer.
Synthesis
L-homoserine(626-72-2) is biosynthesized from L-aspartate, which is synthesized from oxaloacetate, a TCA cycle intermediate. Homoserine is activated through esterification to form the O-acetyl ester by the enzyme homoserine O-acetyltransferase. In certain organisms, including the yeast Saccharomyces cerevisiae and certain bacteria, hydrogen sulfide reacts with O-acetyl-L-homoserine, replacing the acetyl group and forming L-homocysteine.
Purification Methods
The acid (3g) is dissolved in freshly boiled H2O (30mL) under N2, cooled under N2 (all operations should be under N2), absolute EtOH (100mL) is added, the acid is filtered off, and a second crop is obtained by diluting the filtrate to 500mL with absolute EtOH, kept overnight in a refrigerator, filtered, washed with EtOH and dried in a vacuum. The D(R,R)-form has similar properties but is –ve in M HCl and +ve in H2O. [du Vigneaud & Patterson J Biol Chem 109 101 1935, du Vigneaud & Brown Biochemical Preparations 5 93, 95 1975, Greenstein & Winitz The Chemistry of the Amino Acids J. Wiley, Vol 3 pp 2667-2670 1961, Beilstein 4 III 1643, 4 IV 3199, Koegel et al. J Am Chem Soc 77 5708 1955.]

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