(2R)-2-amino-4-carbamoylbutanoic acid

• ChemBase编号: 1931
• 分子式: C5H10N2O3
• 平均质量: 146.1445
• 单一同位素质量: 146.06914219
• SMILES: N[C@H](CCC(=O)N)C(=O)O
• Canonical SMILES: NC(=O)CC[C@H](C(=O)O)N
• InChI: InChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)/t3-/m1/s1
• InChIKey: ZDXPYRJPNDTMRX-GSVOUGTGSA-N

名称和登记号

名称

• IUPAC标准名: (2R)-2-amino-4-carbamoylbutanoic acid
• IUPAC传统名: D-glutamine
• 别名: D-Glutamic acid 5-amide; D-2-Aminoglutaramic acid; D-Glutamine; D-Glutamine

登记号

• CAS号: 5959-95-5
• MDL号: MFCD00065607
• Beilstein号: 1723796
• PubChem SID: 24872875; 24895357; 160965386; 46508385
• PubChem CID: 5961; 145815

理论计算性质

JChem

• Acid pKa: 2.1471426
• 质子受体: 4
• 质子供体: 3
• LogD (pH = 5.5): -4.001106
• LogD (pH = 7.4): -4.0058823
• Log P: -4.0011334
• 摩尔折射率: 33.1099 cm^3
• 极化性: 13.317601 Å^3
• 极化表面积: 106.41 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: -3.32
• LOG S: -0.17
• 溶解度: 9.78e+01 g/l

分子性质

理化性质

• 比旋光度: [α]20/D -34±2°, c = 5% in 5 M HCl

安全信息

• 保存条件: -20°C; Room Temperature (15-30°C)
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

产品相关信息

• 纯度: ≥98% (TLC); ≥98.5% (NT); 97%
• 成盐信息: Free Base
• 燃烧残渣: ≤0.05% (as SO4)
• 干燥失重: ≤0.05% loss on drying, 20 °C (HV)
• Empirical Formula (Hill Notation): C5H10N2O3

详细说明

MP Biomedicals - 02101801

Crystalline

DrugBank - DB02174

• Drug Groups: experimental
• Description: A non-essential amino acid present abundantly throughout the body and is involved in many metabolic processes. It is synthesized from glutamic acid and ammonia. It is the principal carrier of nitrogen in the body and is an important energy source for many cells. [PubChem]

Selleck Chemicals - S1893

Research Area

• Description: Metabolic Disease

Biological Activity

• Description: D-glutamine is a D type stereoisomer of glutamine which is one of the 20 amino acids encoded by the standard genetic code.
• In Vitro: In catabolic states of injury and illness, glutamine becomes conditionally-essential (requiring intake from food or supplements). Glutamine is the most abundant naturally occurring, non-essential amino acid in the human body and one of the few amino acids that can directly cross the blood–brain barrier. ^[1] Glutamine is a key pharmaconutrient in the body's response to stress and injury. Glutamine exerts its protective effects via multiple mechanisms, including direct protection of cells and tissue from injury, attenuation inflammation, and preservation of metabolic function. ^[1]
• In Vivo: Glutamine shows the greatest benefit when administered at doses greater than 0.35 g/kg/day, with optimal benefit potentially occurring at 0.5 g/kg/day. ^[2]

References

• References: [1] Lee WJ, et al. Am J Physiol, 1998, 274(4 Pt 1), C1101-C1107.
• References: [2] Kim M, et al. World Rev Nutr Diet, 2013, 105, 90-96.

Sigma Aldrich - G9003

Other Notes
Unnatural isomer of glutamine

Sigma Aldrich - 49410

Other Notes
Unnatural isomer of glutamine

参考文献

• Lee WJ, et al. Am J Physiol, 1998, 274(4 Pt 1), C1101-C1107.
• Kim M, et al. World Rev Nutr Diet, 2013, 105, 90-96.