苄基N-[(1S)-2-氨基-1-(羟基甲基)-2-氧代-乙基]氨基甲酸酯 | 70897-15-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 苄基N-[(1S)-2-氨基-1-(羟基甲基)-2-氧代-乙基]氨基甲酸酯
• 英文名称: N-α-carbobenzoxy-L-serinamide
• 英文别名: Z-Ser-NH₂；(S)-Benzyl (1-amino-3-hydroxy-1-oxopropan-2-yl)carbamate；benzyl N-[(2S)-1-amino-3-hydroxy-1-oxopropan-2-yl]carbamate
• CAS: 70897-15-3
• 化学式: C₁₁H₁₄N₂O₄
• 分子量: 238.243
• InChiKey: NGEWHDOZPGSSLG-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2924299090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Z-Ser-nh2
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: Z-Ser-nh2
CAS number: 70897-15-3

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C11H14N2O4
Molecular weight: 238.2

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  苄基N-[(1S)-2-氨基-1-(羟基甲基)-2-氧代-乙基]氨基甲酸酯 在 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 1.08h， 生成 N-苄氧羰基甘氨酰胺
  参考文献：
  名称：

  β - O-甲苯磺酰基脱氢丝氨酸作为脱氢氨基酸的前体的合成与表征

  摘要：

  通过用对甲苯磺酰氯活化的二甲基亚砜氧化相应的丝氨酸衍生物1，直接制备β - O-甲苯磺酰基脱氢丝氨酸3。烯醇甲苯磺酸酯3保留了醛的反应性特征，如对于相应的脱氢丝氨酸衍生物2所预期的那样。的典型反应3包括与亲核试剂如伯胺和仲胺的甲苯磺酰基的取代，导致其他脱氢酸。

  DOI：

  10.1016/s0040-4039(97)10360-4
• 作为产物：
  描述：

  N-苄氧羰酰基-L-丝氨酸甲酯 在 氨 作用下， 以 甲醇 为溶剂， 以82%的产率得到苄基N-[(1S)-2-氨基-1-(羟基甲基)-2-氧代-乙基]氨基甲酸酯
  参考文献：
  名称：

  Protein Backbone Modification by Novel C.alpha.-C Side-Chain Scission

  摘要：

  alpha-Ketoamide (-NH-CO-CO-) units in intact peptides are generated from Ser/Thr residues via Ru(VIII)catalyzed C-alpha-C side-chain scission. Facets associated with this novel cu-carbon modification have been probed with 75 peptides chosen to represent every possible peptide environment. The reactions were carried out at room temperature with in situ generated Ru(VIII) in biphasic (CH3CN/CCl4/pH 3 phosphate buffer, 1:1:2 v/v) medium. Whereas Ser/Thr residues placed at the C-terminal end in peptides undergo N-C bond scission leading to des-Ser/Thr peptide amides-thus acting as Gly equivalents in simulating the alpha-amidating action of pituitary enzymes-those located at the N-terminal or nonterminal or even at the C-terminal position (protected as amide) were found to undergo oxidative C-C bond scission (involving C-alpha and C side-chain bond), resulting in the generation of alpha-ketoamide (-NH-CO-CO-) units in the intact peptide backbone. The difference in the products arising from C-alpha-C side-chain scission of Ser/Thr esters and amides is rationalized on the basis of a common mechanism involving either oxaloesters [Pep-NH-CO-COX; X = OMe] or oxalamides [X = NH2 or NH-Pep] arising from the oxidation of initially formed carbinolamide intermediates [Pep-NH-CH(OH)-COX],wherein, while the former are shown to undergo hydrolysis to terminal amides [Pep-NH2], the oxalamides are found to be stable to hydrolysis. Ancillary noteworthy findings are those of peptide bond scission when contiguous Ser-Ser/Thr-Thr residues are present and the oxidative cleavage at C-terminal Tyr/Trp sites generating des amides. The oxidative methodology presented here is mild, simple, and practical and proceeds with chiral retention. The insensitivity of a large number of amino acid residues, such as Gly, Ala, Leu, Asn, Gln, Asp, Glu, Pro, Arg, Phe, Lys, Val, and Aib, and N-protecting groups, such as Boc, Z, and Bz, toward Ru(VIII) under the experimental conditions should make this methodology practical and useful. Sulfur-containing amino acids Cys and Met get oxidized to sulfones in the products.

  DOI：

  10.1021/ja00094a008

文献信息

• Conversion of serine to stereochemically pure .beta.-substituted .alpha.-amino acids via .beta.-lactones
  作者：Lee D. Arnold、Thomas H. Kalantar、John C. Vederas

  DOI：10.1021/ja00310a058

  日期：1985.11

  Lactonisation de serines suivie d'une reaction avec differents nucleophiles. Obtention d'amino-3 alanines, O-acetyl serine, S-benzylcysteine et halogeno-3 alanines

  Lactonisation de serines suvie d'une 反应 avec 不同的亲核试剂。获得 d'amino-3 丙氨酸、O-乙酰丝氨酸、S-苄基半胱氨酸和卤代-3 丙氨酸
• Branched amides of L-aspartyl-D-amino acid dipeptides
  申请人：Pfizer Inc.

  公开号：US04454328A1

  公开（公告）日：1984-06-12

  Amides of L-aspartyl-D-amino acid dipeptides of the formula ##STR1## and physiologically acceptable cationic and acid addition salts thereof wherein R.sup.a is CH.sub.2 OH or CH.sub.2 OCH.sub.3 ; R is a branched member selected from the group consisting of fenchyl, diisopropylcarbinyl, d-methyl-t-butylcarbinyl, d-ethyl-t-butylcarbinyl, di-t-butylcarbinyl, 2-methylthio-2,4-dimethylpentan-3-yl, ##STR2## where at least one of R.sup.3, R.sup.4, R.sup.5, R.sup.6 is alkyl having from one to four carbon atoms and the remainder are hydrogen or alkyl having from one to four carbon atoms, X is O, S, SO, SO.sub.2, C.dbd.O or CHOH; m is zero or 1-4, n and p are each zero, 1, 2 or 3 where the sum of n+p is not greater than 3 and the sum of the carbon atoms in R.sup.3, R.sup.4, R.sup.5 and R.sup.6 is not greater than six, and when both of R.sup.3 and R.sup.4 or R.sup.5 and R.sup.6 are alkyl they are methyl or ethyl, ##STR3## where one of R.sup.7, R.sup.8, R.sup.9 is alkyl having from one to four carbon atoms and the remainder are hydrogen or alkyl having from one to four carbon atoms and the sum of the carbon atoms in R.sup.7, R.sup.8 and R.sup.9 is not greater than six, m and q are the same or different and each have the values previously defined for m; ##STR4## where each of R.sup.12 and R.sup.13 are methyl or ethyl, or R.sup.12 is hydrogen and R.sup.13 is alkyl having from one to four carbon atoms, Z is O or NH and t is 1 or 2, ##STR5## where W is 1-4, R.sup.14 and R.sup.16 are each alkyl having from one to four carbon atoms, R.sup.15 is H, OH, methyl or ethyl and the sum of the carbon atoms in R.sup.14, R.sup.15 and R.sup.16 is not greater than six and when both of R.sup.14 and R.sup.15 are alkyl they are methyl or ethyl, and ##STR6## where R.sup.17 and R.sup.19 are alkyl having from one to four carbon atoms, R.sup.18 and R.sup.20 are H or alkyl having one to two carbon atoms, A is OH and B is H, OH or CH.sub.3 and taken together A and B are ##STR7## where the sum of the carbon atoms in R.sup.17, R.sup.18, R.sup.19 and R.sup.20 is not greater than six and when both of R.sup.17 and R.sup.18 or R.sup.19 and R.sup.20 are alkyl they are methyl or ethyl; said amides are potent sweeteners having advantages over the prior art, edible compositions containing them, methods for their use in edible compositions and novel amide intermediates useful in their production.

  L-天冬氨酸-D-氨基酸二肽的酰胺，其化学式为##STR1##及其生理上可接受的阳离子和酸盐，其中R.sup.a为CH.sub.2 OH或CH.sub.2 OCH.sub.3；R为从茴香基、二异丙基甲基、d-甲基-t-叔丁基甲基、d-乙基-t-叔丁基甲基、二-t-叔丁基甲基、2-甲硫基-2,4-二甲基戊烷-3-基，##STR2##中选择的支链成员，其中R.sup.3、R.sup.4、R.sup.5、R.sup.6中至少有一个是具有一到四个碳原子的烷基，其余为氢或具有一到四个碳原子的烷基，X为O、S、SO、SO.sub.2、C.dbd.O或CHOH；m为零或1-4，n和p分别为零、1、2或3，其中n+p的总和不大于3，R.sup.3、R.sup.4、R.sup.5和R.sup.6中的碳原子总和不大于六，当R.sup.3和R.sup.4或R.sup.5和R.sup.6中的两个均为烷基时，它们为甲基或乙基，##STR3##其中R.sup.7、R.sup.8、R.sup.9中的一个是具有一到四个碳原子的烷基，其余为氢或具有一到四个碳原子的烷基，R.sup.7、R.sup.8和R.sup.9中的碳原子总和不大于六，m和q相同或不同，且具有先前定义的m的值；##STR4##其中R.sup.12和R.sup.13中的每一个均为甲基或乙基，或R.sup.12为氢且R.sup.13为具有一到四个碳原子的烷基，Z为O或NH，t为1或2，##STR5##其中W为1-4，R.sup.14和R.sup.16均为具有一到四个碳原子的烷基，R.sup.15为H、OH、甲基或乙基，R.sup.14、R.sup.15和R.sup.16中的碳原子总和不大于六，当R.sup.14和R.sup.15均为烷基时，它们为甲基或乙基，以及##STR6##其中R.sup.17和R.sup.19为具有一到四个碳原子的烷基，R.sup.18和R.sup.20为H或具有一到二个碳原子的烷基，A为OH，B为H、OH或CH.sub.3，A和B一起为##STR7##其中R.sup.17、R.sup.18、R.sup.19和R.sup.20中的碳原子总和不大于六，当R.sup.17和R.sup.18或R.sup.19和R.sup.20中的两个均为烷基时，它们为甲基或乙基；所述酰胺是具有优于先前技术的优点的强甜味剂，包含它们的可食用组合物，其在可食用组合物中的使用方法以及在其生产中有用的新型酰胺中间体。
• Enzymatic C-terminal amidation of amino acids and peptides
  作者：Timo Nuijens、Elena Piva、John A.W. Kruijtzer、Dirk T.S. Rijkers、Rob M.J. Liskamp、Peter J.L.M. Quaedflieg

  DOI：10.1016/j.tetlet.2012.05.039

  日期：2012.7

  enzymatic approaches for the conversion of semi-protected amino acid and peptidyl C-terminal α-carboxylic acids into their corresponding amides. In the first approach, the lipase Candida antarctica lipase-B (Cal-B), and in the second approach, the protease Subtilisin A, are used, respectively. We found that by using the ammonium salt of the α-carboxylic acid instead of separate ammonia sources, the enzymatic

  在本文中，我们描述了两种通用且高产的酶促方法，可将半保护的氨基酸和肽基C末端α-羧酸转化为它们相应的酰胺。在第一种方法中，分别使用脂肪酶南极假丝酵母脂肪酶-B（Cal-B），在第二种方法中，分别使用蛋白酶枯草杆菌蛋白酶A。我们发现，通过使用α-羧酸的铵盐代替单独的氨源，酶促酰胺化反应的进行速度大大加快，而没有副反应，并且使产物收率接近定量。
• Synthesis of α,β-Dehydrotryptophan by reaction of indole with the β-(N-methylamino)dehydroalanine derivative
  作者：Takashi Nakazawa、Masako Ishii、Hans-Jürgen Musiol、Luis Moroder

  DOI：10.1016/s0040-4039(97)10850-4

  日期：1998.3

  α,β-Dehydrotryptophan 4 is synthesized by a sequence of reactions starting with the corresponding serine derivative 1. This procedure includes substitution reaction between indole and the methylamino group of the β-(N-methylamino)dehydroalanine derivative 3 in acetic acid. The key intermediate 3 is obtained by oxidation of 1 with dimethylsulfoxide activated by p-toluenesulfonyl chloride, followed by

  α，β-脱氢色氨酸4是通过从相应的丝氨酸衍生物1开始的一系列反应合成的。该步骤包括在乙酸中吲哚与β-（N-甲基氨基）脱氢丙氨酸衍生物3的甲基氨基之间的取代反应。通过用对甲苯磺酰氯活化的二甲基亚砜将1氧化，然后使所得的β - O-甲苯磺酰基脱氢丝氨酸2与甲胺反应，得到关键中间体3。
• Acceptor-Controlled Transfer Dehydration of Amides to Nitriles
  作者：Hiroyuki Okabe、Asuka Naraoka、Takahiro Isogawa、Shunsuke Oishi、Hiroshi Naka

  DOI：10.1021/acs.orglett.9b01657

  日期：2019.6.21

  dehydration of primary amides to nitriles efficiently proceeds under mild, aqueous conditions via the use of dichloroacetonitrile as a water acceptor. A key to the design of this transfer dehydration catalysis is the identification of an efficient water acceptor, dichloroacetonitrile, that preferentially reacts with amides over other polar functional groups with the aid of the Pd catalyst and makes the desired

  通过使用二氯乙腈作为水受体，在温和的水性条件下钯催化的伯酰胺脱水有效地进行为腈。设计该转移脱水催化的关键是确定一种有效的水受体二氯乙腈，该水受体在Pd催化剂的帮助下优先于酰胺而不是其他极性官能团反应，并使所需的反应体系趋于能动，从而驱动脱水。