CHUYN 9 L THUYT AMIN AMINOAXIT PROTEIN CHUYN 9 L THUYT AMIN AMINOAXIT PROTEIN I KHI NIM, PHN LOI, DANH

I, DANH PHP V NG PHN 1. Khi nim Amin l hp cht hu c c to ra khi th mt hoc nhiu nguyn t hiro trong phn t amoniac bng mt hoc nhiu gc hirocacbon. V d:

2. Phn loi Amin c phn loi theo hai cch thng dng nht: a) Theo c im cu to ca gc hirocacbon: amin thm, amin bo, amin d vng. V d:

b) Theo bc ca amin: Bc amin: l s nguyn t H trong phn t NH3 b thay th bi gc hirocacbon. Theo , cc amin c phn loi thnh: amin bc 1, bc 2, bc 3. V d:

3. Danh php a) Cch gi tn theo danh php gc chc : ank + yl + amin b) Cch gi tn theo danh php thay th : ankan + v tr + amin c) Tn thng thng ch p dng vi mt s amin Hp cht CH3NH2 CH3CH(NH2)CH3 CH3NHC2H5 CH3CH(CH3)CH2NH2 CH3CH2CH(NH2)CH3 (CH3)3CNH2 CH3NHCH2CH2CH3 CH3NHCH(CH3)2 C2H5NHC2H5 (CH3)2NC2H5 C6H5NH2 Ch : - Tn cc nhm ankyl c theo th t ch ci a, b, c - Vi cc amin bc 2 v 3, chn mch di nht cha N lm mch chnh, N c ch s v tr nh nht. t mt nguyn t N trc mi nhm th ca amin - Khi nhm NH2 ng vai tr nhm th th gi l nhm amino. V d: CH3CH(NH2)COOH (axit 2-aminopropanoic) 4. ng phn Amin c cc loi ng phn: -1Tn gc chc metylamin isopropylamin etylmetylamin isobutylamin sec-butylamin tert-butylamin metylpropylamin isopropylmetylamin ietylamin etylimetylamin phenylamin Tn thay th metanamin propan-2-amin N-metyletanamin 2-metylpropan-1-amin butan-2-amin 2-metylpropan-2-amin N-metylpropan-1-amin N-metylpropan-2-amin N-etyletanamin N,N-imetyletanamin benzenamin Tn thng

anilin

CHUYN 9 L THUYT AMIN AMINOAXIT PROTEIN - ng phn v mch cacbon: - ng phn v tr nhm chc - ng phn v bc ca amin II TNH CHT VT L - Metyl, imetyl, trimetyl v etylamin l nhng cht kh c mi khai kh chu, c, d tan trong nc, cc amin ng ng cao hn l cht lng hoc rn - Anilin l cht lng, nhit si l 184oC, khng mu, rt c, t tan trong nc, tan trong ancol v benzen III CU TO PHN T V SO SNH LC BAZ 1. Cu trc phn t ca amoniac v cc amin

2. Cu to phn t ca amoniac v cc amin

Trn nguyn t nit u c cp electron t do nn amoniac v cc amin u d dng nhn proton. V vy amoniac v cc amin u c tnh baz. 3. c im cu to ca phn t anilin - Do gc phenyl (C6H5) ht cp electron t do ca nit v pha mnh, s chuyn dch electron theo hiu ng lin hp p p (chiu nh mi tn cong) lm cho mt electron trn nguyn t nit gim i, kh nng nhn proton gim i. Kt qu l lm cho tnh baz ca anilin rt yu (khng lm xanh c qu tm, khng lm hng c phenolphtalein). - Nhm amino (NH2) lm tng kh nng th Br vo gc phenyl (do nh hng ca hiu ng +C). Phn ng th xy ra cc v tr ortho v para do nhm NH2 y electron vo lm mt electron cc v tr ny tng ln 4. So snh lc baz a) Cc yu t nh hng n lc baz ca amin: - Mt electron trn nguyn t N: mt cng cao, lc baz cng mnh v ngc li - Hiu ng khng gian: gc R cng cng knh v cng nhiu gc R th lm cho tnh baz gim i, ph thuc vo gc hirocacbon. V d tnh baz ca (CH3)2NH > CH3NH2 > (CH3)3N ; (C2H5)2NH > (C2H5)3N > C2H5NH2 b) Phng php Gc y electron lm tng tnh baz, gc ht electron lm gim tnh baz. V d: p-NO2-C6H4NH2 < C6H5NH2 < NH3 < CH3NH2 < C2H5NH2 < C3H7NH2 IV TNH CHT HA HC -2-

CHUYN 9 L THUYT AMIN AMINOAXIT PROTEIN 1. Tnh cht ca chc amin a) Tnh baz: tc dng ln giy qu tm m hoc phenolphtalein v tc dng vi axit - Dung dch metylamin v nhiu ng ng ca n c kh nng lm xanh giy qu tm hoc lm hng phenolphtalein do kt hp vi proton mnh hn amoniac - Anilin v cc amin thm rt t tan trong nc. Dung dch ca chng khng lm i mu qu tm v phenolphtalein

b) Phn ng vi axit nitr: - Amin no bc 1 + HNO2 ROH + N2 + H2O. V d: C2H5NH2 + HONO C2H5OH + N2 + H2O - Amin thm bc 1 tc dng vi HNO2 nhit thp to thnh mui iazoni. V d: C6H5NH2 + HONO + HCl C6H5N2+ Cl- + 2H2O benzeniazoni clorua

c) Phn ng ankyl ha: amin bc 1 hoc bc 2 tc dng vi ankyl halogenua (CH3I, .) Phn ng ny dng iu ch amin bc cao t amin bc thp hn. V d: C2H5NH2 + CH3I C2H5NHCH3 + HI d) Phn ng ca amin tan trong nc vi dung dch mui ca cc kim loi c hiroxit kt ta 3CH3NH2 + FeCl3 + 3H2O Fe(OH)3 + 3CH3NH3Cl 2. Phn ng th nhn thm ca anilin

V - NG DNG V IU CH 1. ng dng (SGK ha hc nng cao lp 12 trang 60) 2. iu ch a) Thay th nguyn t H ca phn t amoniac Ankylamin c iu ch t amoniac v ankyl halogenua. V d: -3-

CHUYN 9 L THUYT AMIN AMINOAXIT PROTEIN

b) Kh hp cht nitro Anilin v cc amin thm thng c iu ch bng cch kh nitrobenzen (hoc dn xut nitro tng ng) bi hiro mi sinh nh tc dng ca kim loi (nh Fe, Zn) vi axit HCl. V d:

Hoc vit gn l:

Ngoi ra, cc amin cn c iu ch bng nhiu cch khc AMINO AXIT I NH NGHA, CU TO, PHN LOI V DANH PHP 1. nh ngha - Amino axit l loi hp cht hu c tp chc m phn t cha ng thi nhm amino (NH2) v nhm cacboxyl (COOH) - Cng thc chung: (H2N)x R (COOH)y 2. Cu to phn t - Trong phn t amino axit, nhm NH2 v nhm COOH tng tc vi nhau to ion lng cc. V vy amino axit kt tinh tn ti dng ion lng cc - Trong dung dch, dng ion lng cc chuyn mt phn nh thnh dng phn t

3. Phn loi Da vo cu to gc R phn 20 amino axit c bn thnh cc nhm. Mt trong cc cch phn loi l 20 amino axit c phn thnh 5 nhm nh sau: a) Nhm 1: cc amino axit c gc R khng phn cc k nc, thuc nhm ny c 6 amino axit: Gly (G), Ala (A), Val (V), Leu (L), ILe (I), Pro (P) b) Nhm 2: cc amino axit c gc R l nhn thm, thuc nhm ny c 3 amino axit: Phe (F), Tyr (Y), Trp (W) c) Nhm 3: cc amino axit c gc R baz, tch in dng, thuc nhm ny c 3 amino axit: Lys (K), Arg (R), His (H) d) Nhm 4: cc amino axit c gc R phn cc, khng tch in, thuc nhm ny c 6 amino axit: Ser (S), Thr (T), Cys (C), Met (M), Asn (N), Gln (Q)

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CHUYN 9 L THUYT AMIN AMINOAXIT PROTEIN e) Nhm 5: cc amino axit c gc R axit, tch in m, thuc nhm ny c 2 amino axit: Asp (D), Glu (E) 4. Danh php a) Tn thay th: axit + v tr + amino + tn axit cacboxylic tng ng. V d: H2NCH2COOH: axit aminoetanoic ; HOOC[CH2]2CH(NH2)COOH: axit 2-aminopentanioic b) Tn bn h thng: axit + v tr ch ci Hi Lp (, , , , , ) + amino + tn thng thng ca axit cacboxylic tng ng. V d: CH3CH(NH2)COOH : axit -aminopropionic H2N[CH2]5COOH : axit -aminocaproic H2N[CH2]6COOH: axit -aminoenantoic c) Tn thng thng: cc amino axit thin nhin (-amino axit) u c tn thng. V d: H2NCH2COOH c tn thng l glyxin (Gly) hay glicocol II TNH CHT VT L Cc amino axit l cc cht rn khng mu, v hi ngt, d tan trong nc v chng tn ti dng ion lng cc (mui ni phn t), nhit nng chy cao (v l hp cht ion) III TNH CHT HA HC 1. Tnh cht axit baz ca dung dch amino axit a) Tc dng ln thuc th mu: (H2N)x R (COOH)y. Khi: - x = y th amino axit trung tnh, qu tm khng i mu - x > y th amino axit c tnh baz, qu tm ha xanh - x < y th amino axit c tnh axit, qu tm ha b) Tnh cht lng tnh: - Tc dng vi dung dch baz (do c nhm COOH) H2NCH2COOH + NaOH H2NCH2COONa + H2O hoc: H3N+CH2COO + NaOH H2NCH2COONa + H2O - Tc dng vi dung dch axit (do c nhm NH2) H2NCH2COOH + HCl ClH3NCH2COOH hoc: H3N+CH2COO + HCl ClH3NCH2COOH 2. Phn ng este ha nhm COOH

3. Phn ng ca nhm NH2 vi HNO2 H2NCH2COOH + HNO2 HOCH2 COOH + N2 + H2O axit hiroxiaxetic 4. Phn ng trng ngng - Do c nhm NH2 v COOH nn amino axit tham gia phn ng trng ngng to thnh polime thuc loi poliamit - Trong phn ng ny, OH ca nhm COOH phn t axit ny kt hp vi H ca nhm NH2 phn t axit kia to thnh nc v sinh ra polime - V d: -5-

CHUYN 9 L THUYT AMIN AMINOAXIT PROTEIN

V - NG DNG - Amino axit thin nhin (hu ht l -amino axit) l c s kin to nn cc loi protein ca c th sng - Mui mononatri ca axit glutamic c dng lm m chnh (hay bt ngt) - Axit -aminocaproic v axit -aminoenantoic l nguyn liu sn xut t tng hp (nilon 6 v nilon 7) - Axit glutamic l thuc h tr thn kinh, methionin (CH3SCH2CH2CH(NH2)COOH) l thuc b gan PEPTIT V PROTEIN A PEPTIT I KHI NIM V PHN LOI 1. Khi nim Lin kt ca nhm CO vi nhm NH gia hai n v -amino axit c loi l lin kt peptit

Peptit l nhng hp cht cha t 2 n 50 gc -amino axit lin kt vi nhau bng cc lin kt petit 2. Phn loi Cc peptit c phn thnh hai loi: a) Oligopeptit: gm cc peptit c t 2 n 10 gc -amino axit v c gi tng ng l ipeptit, tripeptit b) Polipeptit: gm cc peptit c t 11 n 50 gc -amino axit. Polipeptit l c s to nn protein II CU TO, NG PHN V DANH PHP 1. Cu to v ng nhn - Phn t peptit hp thnh t cc gc -amino axit ni vi nhau bi lin kt peptit theo mt trt t nht nh: amino axit u N cn nhm NH2, amino axit u C cn nhm COOH

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CHUYN 9 L THUYT AMIN AMINOAXIT PROTEIN

- Nu phn t peptit cha n gc -amino axit khc nhau th s ng phn loi peptit s l n! - Nu trong phn t peptit c i cp gc -amino axit ging nhau th s ng phn ch cn 2. Danh php Tn ca peptit c hnh thnh bng cch ghp tn gc axyl ca cc -amino axit bt u t u N, ri kt thc bng tn ca axit u C (c gi nguyn). V d:

III TNH CHT 1. Tnh cht vt l Cc peptit thng th rn, c nhit nng chy cao v d tan trong nc 2. Tnh cht ha hc a) Phn ng mu biure: - Da vo phn ng mu ca biure: H2NCONHCONH2 + Cu(OH)2 phc cht mu tm c trng - Amino axit v ipeptit khng cho phn ng ny. Cc tripeptit tr ln tc dng vi Cu(OH)2 to phc cht mu tm b) Phn ng thy phn: - iu kin thy phn: xc tc axit hoc kim v un nng - Sn phm: cc -amino axit B PROTEIN I KHI NIM V PHN LOI Protein l nhng polipeptit cao phn t c phn t khi t vi chc nghn n vi triu. Protein c phn thnh 2 loi: - Protein n gin: c to thnh ch t cc -amino axit - Protein phc tp: c to thnh t cc protein n gin kt hp vi cc phn t khng phi protein (phi protein) nh axit nucleic, lipit, cacbohirat II TNH CHT CA PROTEIN -7-

CHUYN 9 L THUYT AMIN AMINOAXIT PROTEIN 1. Tnh cht vt l a) Hnh dng: - Dng si: nh keratin (trong tc), miozin (trong c), fibroin (trong t tm) - Dng cu: nh anbumin (trong lng trng trng), hemoglobin (trong mu) b) Tnh tan trong nc: Protein hnh si khng tan, protein hnh cu tan c) S ng t: L s ng li ca protein v tch ra khi dung dch khi un nng hoc thm axit, baz, mui 2. Tnh cht ha hc a) Phn ng thy phn: - iu kin thy phn: xc tc axit hoc kim v un nng hoc xc tc enzim - Sn phm: cc -amino axit b) Phn ng mu:

III KHI NIM V ENZIM V AXIT NUCLEIC 1. Enzim Hu ht c bn cht l protein, xc tc cho cc qu trnh ha hc c bit l trong c th sinh vt. Enzim c gi l cht xc tc sinh hc v c c im: - Tnh chn lc (c hiu) cao: mi enzim ch xc tc cho mt phn ng nht nh - Hot tnh cao: tc phn ng nh xc tc enzim rt cao, gp 109 1011 cht xc tc ha hc 2. Axit nucleic Axit nucleic l mt polieste ca axit photphoric v pentoz + Nu pentoz l riboz, axit nucleic k hiu ARN + Nu pentoz l eoxiriboz, axit nucleic k hiu ADN + Phn t khi ADN t 4 8 triu, thng tn ti dng xon kp + Phn t khi ARN nh hn ADN, thng tn ti dng xon n

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CHUYN 9 L THUYT AMIN AMINOAXIT PROTEIN

MT S CH KHI GII BI TP 1. Mt s dng bi tp hay hi: a) So snh lc baz ca cc amin b) m ng phn amin, amino axit, peptit c) Xc nh cng thc phn t amin, amino axit theo phn ng chy d) Xc nh cng thc phn t amin theo phn ng vi dung dch axit hay dung dch mui e) Xc nh cng thc phn t amino axit theo phn ng axit baz f) Xc nh cng thc cu to ca hp cht g) Phn bit tch cc cht 2. Mt s cng thc hay dng: a) Cng thc phn t ca amin: - Amin n chc: CxHyN (y 2x + 3) - Amin n chc no: CnH2n + 1NH2 hay CnH2n + 3N - Amin a chc: CxHyNt (y 2x + 2 + t) - Amin a chc no: CnH2n + 2 z(NH2)z hay CnH2n + 2 + zNz - Amin thm (ng ng ca anilin): CnH2n 5N (n 6) b) Cng thc phn t CxHyO2N c cc ng phn cu to mch h thng gp: - Amino axit H2NRCOOH - Este ca amino axit H2NRCOOR - Mui amoni ca axit ankanoic RCOONH4 v RCOOH3NR - Hp cht nitro RNO2 c) Cng thc hay dng:

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CHUYN 9 L THUYT AMIN AMINOAXIT PROTEIN - Cng thc bt bo ha (s lin kt + v) ca CxHyNt: = - Cng thc bt bo ha (s lin kt + v) ca CxHyOzNt: = Cng thc ch ng khi gi thit tt c cc lin kt u l lin kt cng ha tr, i vi hp cht ion th cng thc khng cn ng na. V d CH3COONH4 c = nhng trong phn t CH3COONH4 lun 1 lin kt - Nu phn t peptit cha n gc -amino axit khc nhau th s ng phn loi peptit s l n! - Nu trong phn t peptit c i cp gc -amino axit ging nhau th s ng phn ch cn 3. Mt s phn ng cn lu 3CnH2n + 3N + FeCl3 + 3H2O Fe(OH)3 + 3CnH2n + 4NCl (H2N)x R(COOH)y + xHCl (ClH3N)x R(COOH)y (ClH3N)x R(COOH)y + (x + y)NaOH (H2N)x R(COONa)y + xNaCl + (x + y)H2O (H2N)x R(COOH)y + yNaOH (H2N)x R(COONa)y + yH2O (H2N)x R(COONa)y + (x + y)HCl (ClH3N)x R(COOH)y + yNaCl 2(H2N)x R(COOH)y + xH2SO4 [(H3N)x R(COOH)y]2(SO4)n 2(H2N)x R(COOH)y + yBa(OH)2 [(H2N)x R(COO)y]2Bay + 2yH2O

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