d,l-Serine

Base Information

• Chemical Name: d,l-Serine
• CAS No.: 56-45-1
• Molecular Formula: C3H7NO3
• Molecular Weight: 105.093
• Hs Code.: 2922.49
• Mol file: 56-45-1.mol

Synonyms:(2S)-2-azaniumyl-3-hydroxypropanoate;(2S)-2-ammonio-3-hydroxypropanoate;(+/-) 2-Amino-3-hydroxypropionic acid;d,l-serine;3atp;3-hydroxy-alanine;L-serine III;L-serine zwitterion;3q1x;4b2d;CHEBI:33384;(2S)-2-azaniumyl-3-oxidanyl-propanoate;A820293

Chemical Property of d,l-Serine

Chemical Property:

• Appearance/Colour: White crystalline powder
• Melting Point: 222ºC
• Boiling Point: 394.822 °C at 760 mmHg
• Flash Point: 192.582 °C
• PSA: 83.55000
• Density: 1.416 g/cm³
• LogP: -0.90910
• Water Solubility.: 250 g/L (20℃)
• XLogP3: -2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 105.042593085
• Heavy Atom Count: 7
• Complexity: 67.1

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: S24/25:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(C(C(=O)[O-])[NH3+])O
• Isomeric SMILES: C([C@@H](C(=O)[O-])[NH3+])O
• Role in Cancer Cell Survival: Serine is essential for cancer cell survival, fueled by the glycolysis and glutaminolysis pathways providing precursors 3-phosphoglycerate (3-PG) and glutamate, respectively.; The serine synthesis pathway (SSP) represents a critical point for glucose conversion, with serine contributing to one-carbon metabolism supporting various biosynthetic pathways crucial for cancer cell proliferation and survival.
• Reprogramming of Metabolism in Cancer Cells: Cancer cells undergo metabolic reprogramming to support proliferation and survival, with some subtypes hyperactivating serine and glycine synthesis.; Copy-number amplifications of serine- and glycine-synthesis genes and genetic alterations in oncogenes and tumor-suppressor genes enhance serine and glycine synthesis, supporting oncogenesis.
• Contribution to Important Processes: Serine and glycine contribute to essential processes including protein, nucleotide, and lipid synthesis, antioxidant defense through glutathione and NADPH synthesis, and provision of one-carbon units for the folate cycle and methylation reactions.
• Role in Metabolic Homeostasis and Health: Serine plays a crucial role in maintaining metabolic dynamic homeostasis and health by regulating various biological processes, including nucleotide and lipid metabolism.; Exogenous serine supplementation may be essential to alleviate stress responses under conditions such as oxidative stress or bacterial infection.
• Metabolic Pathways: Serine is a core amino acid in the serine, glycine, and one-carbon pathway (SGOCP), derived from nutrients like proteins and phospholipids. It can be synthesized endogenously from glycine via serine hydroxymethyltransferase (SHMT) or through the serine synthesis pathway (SSP) using 3-phosphoglycerate (3PG) as a precursor.; Serine acts as an activator of pyruvate kinase M2 isoform (PKM2), and its deficiency reduces PKM2 activity, causing increased flow to the SSP.; Negative feedback regulation of the SSP is mediated by 2-phosphoglycerate (2PG), which activates phosphoglycerate dehydrogenase (PHGDH).

Technology Process of d,l-Serine

There total 205 articles about d,l-Serine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 81.0%

→ L-serin (56-45-1,83245-15-2) + N-(9H-fluoren-9-ylmethoxycarbonyl)-L-serine (73724-45-5)

Guidance literature:

Reference yield:

(S)-4-Amino-5-[(2S,3R)-2-((8R,11S)-8-carbamoyl-2,4-dihydroxy-1-methyl-10,14-dioxo-5,7,8,9,10,11,12,14-octahydro-13-oxa-6-thia-9-aza-benzocyclododecen-11-ylcarbamoyl)-3-hydroxy-pyrrolidin-1-yl]-5-oxo-pentanoic acid → L-serin (56-45-1,83245-15-2) + L-Cysteine (52-90-4) + (2S,3R)-3-hydroxyproline (567-35-1,567-36-2,4298-05-9,4298-06-0,4298-08-2,14916-76-8,62182-84-7,104069-26-3,118492-86-7,119677-21-3)

Guidance literature:

With hydrogenchloride; In hydrogenchloride; for 24h; product separation and chiral analysis by HPLC;

DOI:10.7164/antibiotics.50.402

Reference yield:

cyclothialidine (147214-63-9) → L-alanin (56-41-7,25191-17-7,18875-37-1) + L-serin (56-45-1,83245-15-2) + L-Cysteine (52-90-4) + (2S,3R)-3-hydroxyproline (567-35-1,567-36-2,4298-05-9,4298-06-0,4298-08-2,14916-76-8,62182-84-7,104069-26-3,118492-86-7,119677-21-3)

Guidance literature:

With hydrogenchloride; In hydrogenchloride; for 24h; product separation and chiral analysis by HPLC;

DOI:10.7164/antibiotics.50.402

upstream raw materials:

L-serinamide

serin

glyceric acid

benzoyl-DL-serine

Downstream raw materials:

L-Cysteine

L-cystathionine

L-serine benzyl ester

serin

Refernces

• 1、 L'vov,Tochtamysheva,Shashkov,Dmitriev,Capek. "3-[(N-acetyl-L-seryl)amino]-3,6-dideoxy-D-glucose: a novel constituent of a bacterial antigenic polysaccharide.". . p. 233 - 239. Retrieved 1983.
• 2、 MacIntyre, Logan W.,Marchbank, Douglas H.,Correa, Hebelin,Kerr, Russell G.. "Fusaristatin C, a Cyclic Lipodepsipeptide from Pithomyces sp. RKDO 1698". . p. 2768 - 2772. Retrieved 2018.
• 3、 Bian, Xiaoying,Dai, Guangzhi,Jiao, Nianzhi,Liu, Yang,Ravichandran, Vinothkannan,Ren, Xiangmei,Shen, Qiyao,Sui, Haiyan,Zhang, Youming,Zhong, Lin,Zhou, Haibo. "Saccharochelins A-H, Cytotoxic Amphiphilic Siderophores from the Rare Marine Actinomycete Saccharothrix sp. D09". . p. 2149 - 2156. Retrieved 2021/08/20.
• 4、 Chao, Rong,Hou, Xue-Mei,Xu, Wei-Feng,Hai, Yang,Wei, Mei-Yan,Wang, Chang-Yun,Gu, Yu-Cheng,Shao, Chang-Lun. "Targeted Isolation of Asperheptatides from a Coral-Derived Fungus Using LC-MS/MS-Based Molecular Networking and Antitubercular Activities of Modified Cinnamate Derivatives". . p. 11 - 19. Retrieved 2021/01/14.